with Spencer Greenberg
the podcast about ideas that matter

Episode 043: Online and IRL Relationships (with Steve Dean)

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May 20, 2021

To what extent do we put ourselves, each other, and our relationships in fixed, sharply-defined boxes? Do we exude trust to people we meet? How often do we project our own wants and needs onto other people? How do the experiences of men and women differ on dating apps? Why do men behave so badly towards women (both online and in the meatspace)? How can people improve their dating experiences? How do we tell our own stories? And how do we recognize the ways in which our lives and the lives of others can intersect such that everyone is better off? How can we recognize and avoid "takers"?

Steve Dean is an NYC-based dating & relationship coach, researcher, educator, and community builder. He offers dating coaching and experimental events through, and hosts the Dateworking podcast which explores the nuances across relationships in romance, friendships, workplaces, and communities. You can find Steve on Instagram, LinkedIn, Facebook, Medium, and Twitter: @stevenmdean. In his spare time, Steve delights in daylong walks through natural and built environments, punctuated by photography and puppy petting.

JOSH: Hello, and welcome to Clearer Thinking with Spencer Greenberg, the podcast about ideas that matter. I'm Josh Castle, the producer of the podcast, and I'm so glad you've joined us today. In this episode, Spencer speaks with Steve Dean about integrating social interactions across platonic, romantic and professional domains, navigating relationships with varying norms, developing group-oriented approaches to compatibility, and leveraging networks to make meaningful differences for others.

SPENCER: Steve, thanks so much for coming on.

STEVE: Oh, man, it's been too long, Spencer. I love hearing from you and I love talking with you.

SPENCER: I always enjoy talking to you. The first thing I wanted to ask you about is your social life because I find your social life fascinating. And I think people are gonna be really interested in it. Can you tell us a bit about the way you socialize, and all the apps you use to do it?

STEVE: Trying to find out where to start is probably the hardest part of that question. [laughs] Let's start with the moment when COVID struck. That's the best way to understand it because that was when I put a pause on my social life. I've had a lot of time now to reflect on what's changed, and there have been some big changes. Since 2011, I've been nomading around the world. I've hit about 25 cities and every single place that I've lived has been in a context of not having an apartment, not having a place to call my own, and always being in a position where I carry all that I own on my back (in the form of a backpack or a duffel bag). So my social life has been almost this constant evolution of people coming into my life, going out of my life, coming back, meeting other people. It's been almost like a beautiful thing to behold but also, when I look back on the day-to-day, it's an introvert's worst nightmare. I probably met over 10,000 people, many of whom I would see on a regular basis, whether digitally or through in-person events. There were times when I'd be going to events over seven days a week, multiple events per day, from place to place to place. It's like the ultimate New York FOMO but multiplied across. [laughs]

SPENCER: I can't tell you how many times someone has mentioned you in conversation. I'm like, "Oh, you know Steve Dean? Of course, you know Steve Dean," or like, "How did you meet this person?" "Oh, Steve Dean. Of course, it was through Steve Dean." It's just hilarious how many people you meet and how connected you are. Tell me though, on a typical day pre-COVID, how many people would you communicate with?

STEVE: If I told someone in the morning, "I don't want to talk to anyone today," I'd probably talk to about 30 people. That would be a day when I'm having an extremely introverted moment. And it wasn't weird or uncommon for me to talk to over 100 people in a day or more. I could meet 100 people in a day just by hosting a couple different events or attending a few different events. On average, any event that I was hosting, I would invite somewhere between 50 and 500 people, manually just clicking through, if it's a Facebook invite, sometimes through mailing lists.

SPENCER: So you must have met way more than 10,000 people then, actually. I feel like that's a lowball.

STEVE: It's possible.

SPENCER: Okay, well, you've had communication and gone back and forth and so on.

STEVE: Yeah, like LinkedIn connections, Facebook friends, all of those combined, that's where I get that number. But in terms of just people I happen to have met, I have no idea what that number would look like.

SPENCER: Must be huge. Tell me about the way you communicate. Tell me about the apps you use.

STEVE: Yeah, that was the next fun part. This is the part that's driving me crazy now because I'm trying to understand where all of the people I've been communicating with are. Because now that I can't physically see them, I have to rely on their digital tendrils. Where are they now? Are they on Facebook chat? Are they on LinkedIn? Are they on WhatsApp, or Wickr, or WeChat, or any of the other chat apps, and I'm on well over 20. Are they on one of the dating apps that we happen to connect on? And I'm on well over 200 dating apps, so it could be on any of those. So anytime I get a notification, it could be from someone that I know, but I don't necessarily know where they're going to find me because the avenues, the inroads to my attention, number in the many, many hundreds.

SPENCER: How do you even have a day where you think about anything else? If you're talking to 100 people, doesn't that just segment your attention to tiny bits?

STEVE: That's where we get to the COVID problem because, when I suddenly wanted to be in a position where I could do some deep work, some inner reflection — not being just on call 24/7 for any number of people all the time — it was such a paradigm shift for me trying to essentially remove myself, and remove all of these access points from others, because it's very easy for me to wake up in the morning having a set of plans. And then, just based on looking at my messages that I got over the course of that evening while I was asleep, that can set a completely new agenda for the day. Ten different people can message me with different urgencies, or different things that need to get done, or things that they're worried about. Or maybe they're in town suddenly, for the first time in years, and they just found out about it, and they message me saying, "I'm only here for six hours." So being ready to change plans, with seconds' notice, was essentially my default for at least seven of the last ten years, because in many cases, I didn't have an apartment for the following day, or funds to get a hotel the following day. So my standard lifestyle was entirely dependent on being extremely resourceful and extremely open to whatever new input would come. If you don't have the option of having a bed that night, the question then becomes, what is next? What are the next set of choices? Who do you have to talk to? What do you have to find out about, in order to essentially maybe locate a place where you could dog-sit or cat-sit or apartment-sit or find someone — it could be someone that I'm dating — who is free that night and would like me to be over there. Just so, so many different possibilities for where I could be and I had to keep my attention open to all of them.

SPENCER: How often would it be that you actually wouldn't know where you were sleeping that night?

STEVE: On average, that was something that happened at least 1 to 3 times a week for at least five of those seven years.

SPENCER: One of my most memorable conversations with you was, one day I asked you, "Steve, how many people are you seeing?" Because you're polyamorous and, for a lot of people, that wouldn't be a reasonable question, but for you, it seemed like a reasonable question. Your response struck me so much because, if I recall correctly, you said something like, "Well, that's an impossible question to answer. You need to tell me more. Do you mean, how many people am I in love with? How many people am I having sex with? How many people do I sleep in bed with? How many people do I make out with? How many people do I have platonic cuddles with?" And I was like, "Oh my gosh, I never even thought about how complicated a question that is for you." So tell me about your dating life. What's that like?

STEVE: I think there's another fun instance of a pre- and post-COVID divide here. Because post-COVID, I've been just living with one partner, and it's been one of the most surreal experiences to go from exactly what you described: a life in which the types of relationships that I was investing in, that I was nurturing, really ran the gamut. And I had to make a call of (essentially) which partner or partners to try to live with while in quarantine, and how to communicate that to my partners. Luckily though, when COVID began happening and I had to pick one, it was a pretty easy call in that moment, because a lot of my other partners were moving away, going home, or already had people that were committed to moving in with them, or they just wanted to stay completely safe and alone. And so it wasn't that hard a decision for the pandemic. But prior, that's when every single day was almost a new discovery of a type of relationship that can exist. For instance, I have someone I've been seeing for about seven years or so now, and there are times when she's in monogamous relationships with other people. There are times when she's openly seeing several people. There are times when she's just spending time with me and we're essentially creating the situation where it can feel almost like a micro-monogamous setup for the span of a week or a month. That's just one person but we have multiple permutations of what our relationship can look like, based on where we are in life. We live in different cities. We don't necessarily show up in the same cities in the span of a year, so sometimes it can be one, two, or even three years that go by when we're essentially long distance. And so that is just one instance. It's a relationship that involves closeness, like we can talk to each other about anything. We tried to stay up-to-date on where we're living, what we're up to, what are the things we're struggling through. We try to nurture it through occasional video chats, Facebook chats, sending things back and forth on Instagram, finding apps that only the two of us are using. That's just one person. That's a relationship that's ongoing for years, but it's also one that itself has changed.

SPENCER: Constantly in flux.

STEVE: Yeah. And if you ask me, "Who are you seeing right now ?'' The "right now" about that is the most important thing. Because it could be that this person is in a monogamous relationship with someone else right now. So I'm technically not seeing them right now, but it doesn't mean that the friendship isn't there. I think for me, I treat a lot of relationships in a way where the friendship is the cornerstone, the idea that we're going to know each other for a long time and care about each other for as long as we can, and do what we can to make each other's lives a little bit more joyous, or a little bit happier.

SPENCER: Tell me about your 100-year rule, because I think that's a good tie-in here.

STEVE: When I started living nomadically, and essentially not knowing where I'm going to be and constantly meeting people, and obviously, this all tied into my broader career goals. I wanted to focus my 20s on investing in social capital, getting to know everything I can about the people around me, building out really strong communities and networks. Because I figured, you can do financial capital anytime in life. Making money is a thing that people do; everyone has to do it at some point, for the most part. But making friends is something that's a little bit harder and sometimes it takes a lot more time and more nurturing. I figured I'd do that in my 20s, while I had the energy and the stamina, and the flexibility and the desire to get out and meet more people (because I grew up in a one-square-mile town). I came up with this rule early on and it was based on the idea that the people I meet now might not be the right people for me, whether romantically, whether for a job I might apply to, or at a networking event. There might be very few people you ultimately will make a sale with or that you will become a co-founder with. But they're all part of networks. They're all people who are spending their time trying to build up their lives, trying to see who are the people they want to bring in. And the thing that I really quickly noticed, having worked in the dating industry, the recruiting space, working with helping people find apartments and roommates, is that the same people show up in these different kinds of relationships all the time. So the same person who you go on a date with on Friday could be asking you about that open room in your friend's apartment because they might want to move there next week. They could be asking you if you know of a specific hiring manager somewhere in a month's time when they're trying to job hop. And so no matter who we are, we have these different needs around just connecting with others, around finding whether it's a job, an apartment, a roommate, a romantic partner, a new friend, a new community. These are needs that don't go away just because we're not interested in that person right now. They may show up in 10 years, in 20 years, in 100 years, and still be someone we want to support, and someone that we hold a lot of respect for, or maybe who knows us from a time — maybe a darker time in our lives — and they were supportive of us then. We can turn to them some years later, and still feel like there's a trust there, that there's still someone who you want to invest in, you want to continue knowing. Spencer, you and I met how many years ago now, and I feel like we still continuously pop up on each other's radars, whether it is because we're hosting something or a friend tries to introduce us again. [laughs] Or we find another friend who, upon knowing them, might say, "Oh, my God, do you know Spencer?" And so there's just so many different reasons why we have these different relationships of ours. And my overall philosophy is, if you're thinking of compounding returns over time, then it really behooves us to try to make ourselves into people who can be referred, who can be respected, for that 100-year span. How do we orient our activities, our mindsets, our communities, our actions, in such a way that the people we meet consistently refer people back to us, consistently grow in their respect for us over time?

SPENCER: Because you never know how this person is going to connect in your life. Or you might be doing something that they are also doing later, or that they could help you with or you can help them with and so on.

STEVE: Totally. I'll give a couple of just really fun examples that have happened recently. I was talking to someone who was a prospective client, and this person was not ready to start with me, whether for...

SPENCER: Is this for dating consulting, or what was this for?

STEVE: Specifically dating coaching, which I've been transitioning all my work into in the last couple of months. He was not ready to start because I think he just wanted a little bit more support. He had a friend who he wanted to work with. And he was also worried about the price, and so I was just like, "Okay, I still really respect what he's trying to do." I told him, "If and when you're ready, I'm here. And in the meantime, go live your life, do your thing." And maybe a week later, I had someone else book on my calendar saying another person wants to talk about working together. And it turns out that this guy — the one I talked to first — had referred his friend to me. Then in talking to the friend, we realized that doing a joint session with both of them together would allow them both to have it hit their strike zone price-wise, and would cost me no additional time. And so just through that easy referral, it went from being what could have been two missed clients. And instead, it became a really fun and relatively novel dynamic that we get to explore together. And that's on the client frontier. I also think about this on the dating frontier. I cannot tell you the number of times that I've gone on a date with someone and almost instantly determined that, "Oh, we're not compatible but you would be a really good fit for my friend." And then I asked them about it, and I'll essentially steer them toward, "Hey, here's some other people who, based on the way that you showed up here, based on what you talked about, these are the people that I think you would get along with really well, and I want to invite you to come and meet them."

SPENCER: That's so nice, to go on a date and be like, "Okay, we're not compatible, but I think I know someone you might really enjoy meeting." But I guess one question I have about that, is there a concern that the person is gonna be offended because you're implying that you're not interested in them?

STEVE: That's certainly possible. Also, statistically, any person you ever meet is not the right person for you. And so I think the statistical likelihood of someone else they know being the right person is almost always going to be higher, because it's a one versus one plus X, where X is every other person this person will ever meet. So the idea of judging someone harshly or being upset with them for just being the person that they are, that doesn't code to me as being very sensible. When I respect them for who they are, I want them to be honest with me. But at the end of the day, the most important thing is that we're able to offer to one another, essentially all that we will ever be from here. So it's not saying, "I need you to be this for me right now or, peace out, I'll never talk to you again." It's more, "Hey, can we create a space where we can honestly talk about what we want, what we care about, what we need, what we're struggling through, such that we can then become each other's best referral agents going forward for the rest of our lives on any life domain?" And it almost never fails. It's one of those things that comes from such a space of optimism and generosity, that it's hard for someone to say, "Actually no, I don't like you. And I don't like the way you approach this. So I never want to speak to you again." That doesn't really happen.

SPENCER: One thing that I just realized — I think I've literally never had to stop before, even though we've hung out so many times — is that you live such a high-trust existence. With the people you're meeting, you're always willing to help them. You're assuming that they're willing to help you. You're assuming that it's not zero-sum or negative-sum, but that it's positive-sum that you're gonna help them now. At some point, they'll help you and you don't even have to worry about keeping track of favors. You also assume that you'll find somewhere to stay that night, and someone's going to take care of you. But that's fascinating, because many people live the opposite. They assume that interactions are zero-sum and either you're getting something or the other person is. Do you have any comments on that?

STEVE: On one hand, there are certain things that (I can't deny) lead to it being easier to trust people. So for one, just the basic privilege of being a white dude. In American society, there are societal privileges that get conferred, aka people implicitly trust you and listen to what you say, by default. And I think that it's kind of disgusting but it's also a fact of life that I've had to deal with. And that's partly why I really do like elevating the voices around me, of people who don't necessarily look like me. Because it's just too easy to fall back on this idea that people will trust me more because of factors that are entirely outside my control.

SPENCER: Right. That's fair. But I would also add though, that there's something about you that exudes trust in addition to that. For example, I'm also a white guy and I think I exude less trust than you by default. I think that people look at me and they say, "He looks kinda like he's got a resting evil face" or something. And I try to exude trust. I think I'm a trustworthy person. But I don't know, it doesn't come across the same way that you do. What are your thoughts on that?

STEVE: I think a lot of it comes down to story, and one of the things that I find that I typically do that other people don't do as frequently is that I'm willing to tell the story of where I am with very few filters.

SPENCER: You're very open about just, "Here's who I am. Here's what I'm doing."

STEVE: And it makes it easier for someone to get it, and I'll give you an example from a dating app, because there's plenty of dating apps where, if you tell someone, "Hey, I'm really enjoying this conversation right now. But I now have to go hang out with my other two romantic partners, [laughs] and then go have a phone call with a third. And I still want to see you this weekend." If you said that to most people on a dating app, they would say, "What in God's name is your problem? Why are you on this app? I hate you."

SPENCER: Exactly, yeah. How do you make it not upsetting to people and not offensive? I'm really interested in that.

STEVE: A lot of the way I do it is that I think through what is it that this person really wants? What are they trying to signal based on their profile? And also what are the meaningful interactions we could have? Let's say we had just met. Instead of a dating app, let's say it was CouchSurfing, let's say it was LinkedIn. The way that I talk to people, I'm not starting off a message with, "Hey, sexy, you're looking great tonight." I don't lead with something that's indicating my deep romantic interest or sexual interest, because to do that builds up a set of expectations that is unreasonable if my next move is to then break all of those expectations. Instead, I keep my profile always set up across no matter what app I'm on, so that people get a sense that I'm existing in motion, I'm meeting lots of people, I'm thinking through what dating can be, and helping people not just with dating, but also with additional things like roommates and finding meaningful work.

SPENCER: So they get that this is a connector...

STEVE: Yeah.

SPENCER: ...that is looking to connect on many different levels for many different purposes. But do you say in your profiles, "I'm polyamorous," or how do you describe your dating style or approach?

STEVE: Well, I can just read you one of the lines from my Hinge profile. That'll actually give you a pretty clear sense of the way that I present it. Okay, so one of my lines is, "I'm weirdly attracted to people who are natural connectors with worldly and inquisitive minds, who see beauty and joy in every moment, but aren't blind to privilege and inequality." So that's getting at the idea that people are recognizing that there's a lot going on in how people connect, in what kinds of relationships we have. I like people who are more curious than demanding (that's one element of it). And then, to be even more specific, I have another section that says, "I'm looking for someone who is a good cuddler and conversationalist, someone playful, confident, kind-hearted, curious, empathetic. Bonus points if well-versed in ethical non-monogamy."

SPENCER: Okay, so you do put it out there.

STEVE: Yeah, that one's pretty clear. I also have some photos of me from a CBSN interview. So you can see it, there's some professionalism here, in addition to it being a personal profile. And so people aren't looking at this as, "Oh, this guy is definitely looking for a monogamous, committed relationship and only wants to date one person at a time. That's not the expectation set that I'm leading with. And so I think what I really try to stress — and this is for myself, as well as for clients and friends — is the importance of communicating to someone, almost overcommunicating. I want someone to be so well-informed about how I exist in the world and what I'm here for and what I want to be doing, that they can make their own decision of, "Is this a direction that I'd like to go with anyone?" I've literally had people on a first Tinder date, midway through our first drink, start saying, "You know what, I have a roommate who I really think should hire you." So I'm getting referrals that way. I've also had people on first dates be like, "Hey, do you just want to come over and stay with me? I don't even want to hook up. I just want to keep talking about what's going on in the city that we're living in and keep exploring different places together and meet someone. I'm new to the city and I want to get involved in these different communities that you're casually mentioning that you plan to be showing up at events for." That's really the crux of it. I try to communicate to people that I exist within multiple overlapping communities and that, in engaging with me, they're essentially engaging with not just me, the person, but all of the different vectors of individuals and communities that I would then represent and potentially either connect them to, or bring them into anytime that their preferences or their desires overlap with the thing that I happen to be going to.


SPENCER: There's this idea that I call the "Magnetic Box Problem," which is that if people have these different boxes in their mind, like a standard monogamous relationship is one of their boxes. And then maybe they have a box for a polyamorous couple or something like that. And then what happens is, if you are not in any of the boxes — but they only have, let's say, three boxes in their mind — first, they'll try to just stick you in the closest box that they have. And then, if you say, "No, no, no, but that doesn't describe me," or they otherwise come to be convinced that it doesn't describe you, then they just try to shift you to another one of their preexisting boxes. I call it the magnetic box problem because, no matter what you do, you just get stuck in a box, and what you really need to get them to do is to create some kind of new box or (even better) some kind of new continuum, but it's actually very hard to do that. I feel like you're the quintessential case of this because you're so different from the way other people do things. I imagine people must constantly be just sticking you in boxes that don't describe you. Does that happen to you a lot?

STEVE: I do get a lot that it's hard to find an appropriate box. That's certainly one of them because...

SPENCER: Because even 'polyamorous,' I feel, is just not a very good job of describing you.

STEVE: Certainly not. That's one component of my identity perhaps. But I'm living, as I just mentioned before, in a world in which I'm just with one partner every day. Yes, I guess I'm still engaging with my other partners, whether through video chat or texting. But it feels like a weird time to be polyamorous, just given being essentially locationally monogamous or logistically monogamous, given the lockdowns.

SPENCER: Let's say one thing that makes you fundamentally different from other polyamorous people that I know, is that the way you view relationships feels to me like every relationship you have is like a build-your-own relationship. It's like, "Well, in this particular relationship, we're going to cuddle and make out and work together, but that's it. In this other relationship, we're going to feel romantic but we're not going to have sex. And in this third relationship..." It's just like, every one of them is cooked up from scratch — and then also dynamic, like it might change over time — and you're totally fine with that, you're not resistant to that. Whereas, I think for the vast majority of people, they have sexual relationships and non-sexual relationships, and they draw a very sharp distinction between them. And then they also have work relationships, non-work relationships, and maybe occasionally they'll blend together, like they might become friends with their work colleagues. But pretty much, for the most part, there's a firewall between those as well. Do you have any thoughts on that?

STEVE: Yeah, I think this goes back to just how I communicate with people. One of the things that would probably be pretty noteworthy is that, while a lot of people — and especially on dating apps, you'll see this — they basically project onto you what they desire, regardless of what you actually are going through or want. I just had an instance where a friend of mine was telling me how this guy texted her after seven years of not having seen each other (they hooked up seven years ago, one time). He texts her basically saying, "Hey, come below me." And she's like, "What? I don't even know who this number is. Is this spam?" And so she then later found out that it was this random dude who just thought that that was an acceptable thing to say to someone you haven't spoken to in seven years. And this is not at all uncommon. This is essentially the standard female experience on most dating apps: having men project their desires and needs onto you, and then get mad at you when you're not exactly everything that they declared you must be.

SPENCER: Let's talk about that, because you're an expert in dating apps, and I want to hear just briefly about your background in dating apps, and then I want you to tell us about the discrepancy between the typical female experience on dating apps versus a typical male experience.

STEVE: Yeah, I want to go into them. I want to finish this idea of, when it comes to how I talk to other people, on these apps and in person, a lot of what I do is I start by trying to find out where they are right now. Who is this person? What are they motivated by? What do they actually want here? What do their crappy experiences look like, that they're trying not to repeat? What are the things they aspire to be or to do? In getting that information, and even holding space so that someone can share that information, that's already setting me pretty far apart from the norm, when we're in an age (like the current stage of dating apps), where the norm is like, "Hey, you're cute. Let's hook up." If that's what you're getting 9 times out of 10, then it can be really nice to have someone actually take the time to have a conversation about what you've been experiencing and let you hold the floor for a little bit. That's a lot of what I do is: I create and hold space for people. When it comes to my experiences on these dating apps, I started my first-ever dating profile in 2010 on OKCupid and I ended up in a five-and-a-half year relationship with the first person I ever met with. Even before meeting, we had talked on GChat for 40 hours before setting up our first date. I guess I already had in mind this idea that, if you're going to use the internet to meet people, it can be really nice to get to know them reasonably well, so you know you're pretty compatible before you meet. And I've only gotten better at that over time, by setting up a profile so that it can be designed to attract the most compatible people, the people who are looking for the same kind of thing in their lives. But I was dating at the time, in 2010, in a one-square-mile town, and it was not pleasant to be on a dating app in a one-square-mile town, because I'll see maybe three or four people at most on any given app. And then that's it, that's everyone in the town who was using online dating in 2010. So I started going on app after app after app trying to find out who is in my town. Where is their attention living? Which app do I have to go on? How many apps do I have to be on? And after 50, I was getting exhausted. Luckily, I then moved to New York and suddenly, my phone was blowing up all day, because having 50 dating apps in a city like New York meant that it's basically every day, there's a new opportunity to meet someone. And so my early time in New York was spent in a combination of job searching and meeting friends, meeting people for dates, trying to keep everything very low-cost because I was job searching and I had no money. I was essentially helping people with different things in their life in exchange for housing, doing things like dog-sitting, cat-sitting, helping people with tech support, helping people with their dating lives (because I was on so many apps at this point that I had a clearer sense of what apps are working, which ones are not, which ones are worth someone's time, how do you make a profile on them). And so that's really how I got all that started. It was just this original frustration of dating in a tiny town, and then the recognition by my friends that I was spending a lot more attention than they were in this space and so they kept consistently reaching out for more support, which then gave me even more incentive to try even more apps and see which ones would actually work because I didn't want to waste my own time. I had a lot of other priorities at the time, like finding housing, things like that, and finding work. But then I started getting requests from people as they saw me blogging about dating apps. And they were like, "Well, can I pay you for help? Can you coach me? Can you give me a consultation? I'm trying to build an app of my own. I saw that you are on most of the other ones. So what should I do?" And that's kind of where my business and the thing started. My first little foray into entrepreneurship was just helping a variety of different people and companies with either building the apps or using the apps.

SPENCER: Right. The next thing I want to ask you about is the experience of men and women, typically on dating apps and how they differ. You want to talk about that a little bit?

STEVE: Yeah. I mentioned that a lot of women are not getting particularly happy or fun messages. This is a problem that goes even beyond the dating industry itself because, as that example I mentioned goes into, you could have met someone from a dating app but, years later — at that point, they're just a human — it's not like they're the dating app person. They're a person, you have their phone number. The idea that they would still send terrible messages that make you feel awful. This person, by the way, when my friend didn't reply to him, and blocked his number, he then started signing her up for all of these spam messages. The level of spite that's coming from sexually frustrated men, and then being directed at unsuspecting women on the internet, it's just so high and so exhausting. And this is one of the things that a lot of men really don't understand. They don't understand how to just engage in basic empathy or perspective taking. That's a pretty fundamental problem in society and this is not just confined to American society, but it goes deeper because those problems can sometimes be ameliorated a little bit just by having these men exist, like at a house party, where they can at least have some other competing influences. They can see good behavior modeled for them. But on dating apps, you really don't see good behavior modeled for you. How many men get to see well-constructed male profiles? They only see female profiles, unless they're listing themselves as bisexual and usually the problematic men we're dealing with are not doing that. Beyond that, when men are sending messages, they're trying to think of, "Here's a person I'm attracted to. I don't know what they want, really. Their profile doesn't necessarily say too much." A lot of men just default to saying things like, "Hi, you're beautiful." "Hi, how are you?" "Hi, I want to see you." "Hi, can we get a drink?" And what these men don't realize is that every other man is sending the exact same messages. So while their mail inbox may be fundamentally empty, with very few women reaching out to them, that same woman that they may be trying to message does not have an empty inbox. Most women have inboxes that are full. You can receive over 100 messages in a single day on a single app. And a lot of those messages are the same generic "Hey, how are you? Let's get a drink. You're beautiful. I like your smile. I like your hair." It's all of the same generic crap that, most of the time, just reduces women to how men are perceiving them. And it's just a really frustrating and gross behavior that men have not been given any genuine opportunities to learn from, because dating apps aren't designed to help men send better messages, to help them stop being insanely superficial when it comes to how they essentially consume women on the internet.

SPENCER: It also seems like a feedback loop that's very harmful, which is that, if men find that most of their messages don't get responded to, and women find that their inboxes are full of crappy messages, then men invest less and less time in each message because it has low probability of getting responded to, which means that they send even more crappy messages to more people, which means that women's inboxes are even more full of junk. I can see it being a race to the bottom.

STEVE: It gets even worse than that because the messages aren't just crappy. They become more scornful over time. There's men who, at certain points, only just want to get a response — they don't care if it's positive or negative — they just want the attention. And so they'll start sending things that are even more gruesome and aggressive. I once made a female profile when I was in San Francisco. I was trying to check out just what the dating apps in that city are like, how people respond. And I like to see it from the male and female perspective, because it's actually extraordinarily insightful to see what the average female or male profile looks like here and how people message you. And within one hour of making a profile on a dating app there — and it's not to say something about San Francisco. This is a thing about making profiles as a female user — I was already getting (and this is before I even uploaded a photo), I was already getting rape threats.

SPENCER: What? Oh, my gosh.

STEVE: So even putting your little ticker from M to F (male to female) on a dating profile, if you have a female profile, you're already going to start getting targeted by vicious men who do not recognize that they're in a platform where there's real people who are not looking for that kind of attention. It's really scary, and I have to tell my clients, tell my friends...I literally had a friend yesterday reach out to me saying, "Is it okay to travel across a couple states to go see a guy? He says he wants to see me." And I'm like, "Oh, man, this sounds oddly familiar. Is he just trying to get you to come over so he can then have sex with you and then kick you out of his apartment and leave you stranded two states away?" Because that's a thing that you have to watch out for. It's terrifying just how many nefarious actors are out there and, even in the absence of nefarious actors, it's just people who don't know basic internet etiquette, people who don't recognize the problems inherent in the landscape itself. For instance, on that frontier, think of an average guy who goes on a dating app, and he sees a cute girl, he's like, "Okay, I like this person," and he says to his friend, "What should I say?" And what's the friend gonna say, "Oh, tell her she's cute." What do friends tell you in terms of advice? Nothing useful, as it turns out, so he then types, "Hey, you're cute." Sure enough, he and 20 other people that same day sent the same message, "Hey, you're cute." So what are women then supposed to do when they're getting a whole bunch of messages from men who they're (at baseline) kind of frustrated by, or even a little bit scared of. Because if you don't reply to that message, you never know what the next message is going to be. Is it going to be like, "Hey, I hate you. Go kill yourself." Because that's pretty common. Is it going to be like, "I found these other photos of you on the internet. You better respond to me." That kind of shit happens and it's just really frustrating to be a female-identified individual trying to navigate modern dating apps.

SPENCER: That reminds me of the topic of catcalling, which is something we've discussed before. And I actually ran a study where I asked lots and lots of men if they'd ever catcalled in an anonymous survey. And in that survey, about 18% of men said that they had catcalled before and so I actually asked them in the survey to explain why they did it. In the study, there were four main reasons people said that they catcalled. The first, the most common, was that they said they were hoping it would lead to sex, which I'd like to talk to you about in a moment. The second was that they said they did it to show off in front of their friends. The third was that they thought it would get them noticed by the other person or get them attention from the other person. And the fourth was that they wanted to signal to the other person that they found them attractive. I actually have specific quotes from different respondents. So in the first group, for those hoping to get sex, an example was, "I catcalled the girl in a bar. I was horny and drunk." Another example of that was, "Back in the 1990s, when I saw a very attractive woman walking by, I shouted a comment to her remarking on her sexy body. I would have liked to have sex with her." Then the second group, trying to show off for their friends, here's a quote from one of the survey respondents, "I did it leaving a sporting event. I was doing it as a show of confidence for my friends." Another example of that is, "A girl was walking by while I was with my co-workers. I wanted to show off to them." The third category — in order to get noticed by the person or get their attention — one of the quotes was, "I saw a good-looking lady and wanted to get her attention." Another quote from a respondent was, "I yelled, 'Hey, hot stuff' when passing by a person in my automobile. I wanted them to notice me." And then the fourth category, letting the person know that you find them attractive, one example was, "I saw a hot girl while driving to work. I wanted her to know I thought she was attractive." And another example of that was, "I was just letting the girls know I thought they were pretty. They turned and smiled at us." So I'm curious to hear your reaction to that, those different categories.

STEVE: Yeah. Oh, man. There's a lot to react to there. It sounds like what I'm hearing in each of those, there are three major variables, one being loneliness. These men don't necessarily have other sources of inbound attention. It's not like women go out of their way to pay attention to men. Because if you just reflect on what you just said, there's men constantly assailing women, trying to get their attention. These women, it's all they can do to just get through a day without having many different men trying to interfere in their lives.

SPENCER: To that point, I think a lot of men who live in big cities are completely naive about how often women get catcalled. Some women will get catcalled many times in a given day, and I think that their male friends just have no idea this is happening. And part of the reason is because, when those male friends are around, the catcalling mostly disappears. As a man walking with a woman, you're very unlikely to hear catcalling but, as soon as a woman's alone, she just might get catcalled repeatedly.

STEVE: Yeah, that totally is a factor and ties directly in with the experiences online just as much as offline. Men don't have access to women's inboxes so they don't know what women are having to deal with every day, and that leads them to make really idiotic decisions. Catcalling is yet another example. These men are not receiving inbound attention on a regular basis from women, even though they desire it. And so what do they do? They go out of their way to aggressively insert themselves into a woman's life, an unsuspecting woman who did not ask for any of this. So loneliness is one but I think it also goes directly into entitlement, this idea that they're entitled to women's attention, the guy who said, "I catcall her from my car because I wanted her attention," as though this poor woman, just trying to walk home from work, deserved to have some rando in a car. There's how many thousands of people in New York City, for instance, you walk past in a day. if every one of them felt that same degree of entitlement to your time and attention to comment on your body moving through space, it's a sadistic quality that a lot of people are trapped in this belief that, because they find someone attractive, they're therefore entitled to that person's body or to their attention.

SPENCER: And that first category of hoping for sex, that just seems totally delusional to me. I can't imagine that it almost ever actually happens that, by catcalling, someone gets sex. But in the third category of getting noticed or getting attention, that probably does succeed, at least to some degree, especially if they don't mind getting negative attention where the person just seems annoyed at them but at least the person notices that they exist. And so it's interesting to me where, on the one hand, there's the delusion that like, "Oh, yeah, one of these women's gonna turn around and be like, 'Sure, I'll have sex with you,'" which just seems completely implausible. On the other hand, there's this feedback loop of like, well, they do get some form of attention and if they're okay with it being the person being annoyed at them, or smiling, and then walking away as a way to try to defuse the situation — maybe out of feeling afraid or feeling uncomfortable — that actually is giving them what they want, which is unfortunate, because it might encourage them to do it later and because they might feel, "Oh, yeah, that was actually a good experience for me." Any thoughts on that?

STEVE: Yeah. We can turn to a fun study to help explain this idea of the delusional nature of it. You probably know this study even better than I do. It was one where they had a confederate woman and a confederate man go on college campuses, and walk up to random people and say...

SPENCER: Confederate, as in working with the study?

STEVE: Someone working with the study. They'd say to someone, "I've been noticing you around campus and I find you attractive. I'd like to go to bed with you." (I think it was that phrase.) And when the male confederate was saying it to random female-identified people on campus, the response rate was 0%, zero women of anyone asked said, "Of course, I'd like to (having never met you) go sleep with you." Zero percent. When it came to a female confederate saying that to random male-identified people on campus, I believe 50% of them said yes on the spot to going to bed with someone who just walked up to them and asked.

SPENCER: I remember some people in the study were like, "Why do we have to wait till tonight? Why not just do it now?"

STEVE: I think that signals the level of desperation that a lot of men experience for getting access to female attention on one frontier, and also just their profound loneliness that, when someone's showing them positive attention — negative or positive, they want the attention — but if it's positive, then it's that much more likely that they're going to be like, "Oh, wow, this is of course, of course, do you really like me? What?" I don't even see it as...maybe it is part delusional, but I think that it's almost like a shared delusion among a sizable portion of the male population that, if asked to randomly have sex with someone they found attractive who approached them in that moment, the answer would very likely be yes. And for women, that's just simply not a reality because, usually when that's happening, it's because there's an imminent threat.

SPENCER: Well, I just want to comment on that because I think one interpretation of that study is, "Oh, well, women aren't interested in sex." And I think that's the wrong interpretation. I think a lot of women do really enjoy having sex. And on average, there's some evidence that women are maybe less interested in sex than men on average, but there's a lot of variability, and some women are more interested in sex than the average man. But basically, I think what's misleading about that aspect is that zero women saying yes, probably (in my view) has a lot to do with safety and comfort. So if it was a situation where it was a guy they found attractive, and they felt completely safe, I suspect you would get very different responses. What do you think about that?

STEVE: Totally, just even speaking from experience, there've been plenty of times when a friend meets someone on a dating app. And as soon as they meet up they realize, "Oh, things are fine. You check out. This is great," it's not uncommon for me to get a call from a friend saying, "Hey, do you want to come over and join us?'' that kind of a thing where someone is willing to not just meet one person, but even go and meet that person's friends, because they've already cleared those hurdles of safety and comfort.

SPENCER: Wait, sorry, do you mean just to hang out? Or do you mean like for a threesome?

STEVE: Either one, honestly. I think that safety and comfort is just so important for getting someone to be able to open up about what they actually want, because safety and comfort generally comes before sexual desire.

SPENCER: Right, it's like if you think about Maslow's hierarchy — which I think is not a perfect way to think about these things, but it's a useful framework — until you feel like this person is not going to hurt you, you're not even thinking about the sexual aspect, right? You just need the "Okay, I'm safe and comfortable" first. But once that's dealt with, then you can even begin to consider them as a sexual partner. But I would also add that I think some women have just a fear of being judged for being sexual.

STEVE: Oh, yeah. This goes back to misogyny. And I think there's two edges to that story, because it's not just the fear of being judged; it's also the recognition that, in most societies, sex ends when the male-identified person ejaculates. So the likelihood of someone (a female-identified person) even experiencing pleasure during a sexual dynamic is extraordinarily low for a first encounter. There was a study that was trying to suss out, is there an orgasm gap between men and women, and one of the things they noticed is that women, far more often than men, do not experience an orgasm on the first encounter with someone. But once they've had a few encounters, usually by the third or beyond, that's when there starts to be another parity in their orgasm levels. So it takes up to three, four meetings, where someone can actually get to know what it takes to turn a woman on before there's any expectation of the sex being meaningfully good.

SPENCER: That can also reduce the incentive for that one-off hookup, right?

STEVE: That's what I mean, that's exactly it. For most female-identified people, there's no rational basis for presuming that your first encounter with a random person is going to be a good one. Even if there's no rational basis for assuming the first encounter is a good one, if you get someone referred (and this is where a lot of my experience is, just dealing with referrals and friendships), that's where I can — in a heartbeat — if I make a referral to someone, if let's say, a woman comes to me and says, "I'm really horny, and I really want to find someone, but I hate using these dating apps." If I said to them, "I have someone in mind. If you're open, I'll send them over to your place tonight." That kind of thing gets a much higher likelihood of someone saying, "Absolutely, yes, go for it." Because there's already trust that you can make a good faith referral. There's already trust that this person is being meaningfully vetted.

SPENCER: So you'll do that? You'll actually send over like a blind date hookup for people?

STEVE: Yeah, it's something where, if I have two different friends or people I know who want the exact same thing, and all I have to do is connect them in order for both of their days to get meaningfully better, then that's one Facebook message or one text and I suddenly can be known in their life (for the next however many years or decades) as the person who thought to connect them and thought that their lives would be made better by virtue of getting to know one another in whatever way they choose. And I'm not going to say, "You must have sex tonight." That's not the way that I operate. I operate from a perspective of, "You are people who, I think, share several different dimensions of what you're looking for," whether it be that you're in the same phase in life, you've both gone through a breakup recently and you're not looking for another relationship, but you are looking to still explore and get to discover a bit about yourself. Sometimes, you're both only here for a couple of days and so you're not really looking for someone who's looking for a committed relationship, and you're just really looking for a good night, or a good experience. It's really just the extra thought put into, is this the right connection to be made and is this the right time to make it that makes such a big difference. Think of the discrepancy between a thoughtful friend recommendation versus a catcaller who knows nothing about you and just saw your body moving through space.


SPENCER: Steve, tell me a bit about what you help people with when it comes to dating consulting. What are the things you're advising people on? And maybe you could just give a couple of quick tips on how people can be better on dating sites.

STEVE: Sure. Every time I think that I'm narrowing down to a certain niche of dating, coaching and consulting, I just get another experience that expands it further. Just in the past couple of years, I've worked with everyone from 18-year-old gay men in a country where it's illegal to be gay, to 50-plus-year-old women who are trying to find people who are not going to leave them for a 20-year-old. I had a request the other day from someone who is, I believe, 94 and living in Miami. And the questions that people have, it's not just that there's lots of different people experiencing dating troubles, but the struggles are across the board. So you have run-of-the-mill things like people needing help making a good Tinder profile, or coming up with good dating photos because they feel like they're not getting many swipes. Sometimes they are only attracting a certain kind of person, and we have to find out (we have to do almost like diagnostics work and find out) what is it about your profile that's capturing the attention of the people you don't want attention from? How do you guard against that? How do you get more people to reject you, potentially, so that the right people are going to show up and actually follow through?

SPENCER: That's something I have noticed — when I've looked at friends' dating profiles, when they ask me, "Oh, can you give me feedback?" — is it feels like, a lot of times, people don't realize that their profile needs to be directed at the kind of person they want to attract, not what would attract them. Does that make sense?

STEVE: Yeah.

SPENCER: They'll reference things that they would find really appealing. It's like, "Okay, but think for a second about the person you're trying to meet. Would that person find this appealing?" It's like that second order of thinking.

STEVE: It's sometimes just really frustratingly sad to witness. Frequently, I'll have female clients who, in their mind, they're just trying to be perceived as attractive. I feel like people spend so much time trying to approximate what attractiveness looks like in their own little microverse. It could be like, "I need to lose two pounds, and then I'll be attractive," or "I need to be an inch taller, and then I'll be attractive." And it's almost like this toxic parasitic thinking that — I don't know if this is consumerist culture or late-stage capitalist, any number of vectors that cause it — but when people have this idea of what they need to do or change about themselves to become attractive, it frequently is based on just a really inaccurate estimation of what attractiveness is. I'll see, as a recent example, there's a woman who came to me and she had in her profile (I think it was a Bumble profile), it was nine selfies in a row, all of which were exactly the same facial angle with varying amounts of cleavage. And there was nothing to indicate who she is, what she's doing with her life, what makes her someone who's looking...she told me she was looking for a committed monogamous relationship. And yet, all of her profiles were cleavage selfies, all of her photos. And I just couldn't help but wonder, who do you think...walk me through the world in which the person you're looking for sees this and believes that this is someone looking for a committed, monogamous relationship. It just made no sense. There was no effort on her part, no recognition that it really helps to model the world of the people who are going to encounter your profile and try to understand how their engagement with your profile leads to a success case for you.

SPENCER: Right. So it's a perspective-taking exercise. It reminds me of the way in poker — and I'm not a good poker player — but my understanding is that a common mistake that people make when they're learning poker is, let's say their opponent makes a really big bet, they'll have this reaction, like, "Oh, they must have a really good hand." But then if they would actually take the perspective of their opponent for a moment, they would realize that, if they had a really good hand in that situation, they wouldn't make a really big bet. So they're not saying, "Well, what would I do if I was in that position that my opponent's in with a really good hand? I would not make a really big bet." Yet, they're assuming that their opponent has a really good hand. If they embody the mind of the person who they're trying to attract, and then look at their profile, and then say, "Okay, what would be appealing to them?"

STEVE: Yeah, and this is a process that honestly, it does take time for people to get good at. A lot of people start off by potentially just not recognizing that they even could be attractive to another person. There's a lot of very harmful ideologies going around that cause people to hate themselves. Most of the media directed toward women is telling them, "Oh, this is how you get rid of your cellulite because that's unsightly." "This is how you fix your hair." "You have to spend hundreds of dollars on this, or thousands of dollars a year." And it's all of these things directed at women trying to get them to be more attractive. The same kind of things (like boner pills) for guys, that's certainly one of those things that "you must be able to perform at a certain level, otherwise, no one's going to take you seriously." It goes on. No matter who you are, there are some forces trying to tell you that you're not enough and that you need to do different things to become attractive to anyone. And I think that all of that is such a toxic culture that we're in, that makes us not really recognize what things about us are actually attractive to other people. And it doesn't help that the dating apps are structured to be so photocentric. For instance, no matter what men put in their profiles, women still swipe left on that meeting. They dislike them, they say, "I do not want to ever hear from you," over 80% of the time. So roughly 84 to 96% of the time, women are swiping left. So those men who get left-swiped just never get that attention; it's as though they never existed. And so, no matter what they put in their profile, they still end up getting systematically shafted by just the mere system that is so tied to aesthetics, so tied to what you look like and how you present yourself in that first photo, that people only give you a fraction of a second of their attention before they've already made up their minds that they don't want you. And yeah, of course, that leads people into believing, "Maybe I'm not good enough. Maybe I'm not attractive. No one's matching me." And so they again try to find out, how do I become attractive? How do I get these matches? And what I try to tell people is, what's attractive is going to vary for every person you ever meet. You're all going to have different understandings of what attractiveness is, and what matters is who's going to be attractive for you. And sometimes it just does take going on many different dates to be able to learn that. What kinds of people do you gravitate toward? And then, of the people that you find yourself attracted to, what is it about them that you like? And what is it that they're looking for? Because that's what you then put in your photos. You try to tell your story in a way that pulls in the kinds of people who you're most attracted to and engaged with.

SPENCER: That makes a lot of sense. Okay, so as a mathematician, I tend to view everything through a mathematical lens, I can't even help it. And so I have three somewhat mathematical forms of dating advice that I sometimes give, and I would love to get your feedback on them. Do you agree with them? Do you disagree? And then do you have any nuance to add to make them better? How does that sound?

STEVE: Excellent.

SPENCER: So the first is just the observation that if you could double the number of people you meet without reducing the quality — and by quality here, I just mean the quality in terms of what you're looking for in a partner — then on average, you're gonna meet a partner you like twice as fast. My feeling is that, for many people that don't meet that many people, a lot of times it's, in a sense, the easiest thing they can do is just try to double the number of people they meet without sacrificing quality, and that will actually have huge payoffs in terms of making the time to meet that person that they really like in half the time. What are your thoughts on that?

STEVE: While I do agree that it really helps to meet more people — because it just gives you so much more rich information about what you like, what you dislike — it's almost like the idea of killing the Buddha. Don't put things on a pedestal as though they are enlightenment, they are holy, as a lot of men do to women. They put them on this pedestal, they assume that, "Oh, they're perfect in every way." And then the minute they find anything wrong with the woman, they're like, "Oh, she was not perfect. She's terrible." And meeting more people helps you recognize that, "Oh, even the people I originally thought were perfect, are in fact, just as human as every other person." And so it becomes not about believing that they're everything for you, but instead being more realistic about each different person you meet and what they're looking for. So I think it is helpful to meet more people, because it just forces you to update your priors. It forces you to be more specific and what you actually want over time.

SPENCER: I feel like this advice is best for someone that doesn't meet that many people. Let's say you only meet one person who's in your potential target dating demographic or something, once a month. It feels like going from once a month to once every two weeks can be a big win, in my opinion. Whereas, if you're already meeting three or four a week, maybe there's less advantage to that.

STEVE: Yeah. And I think that going back to what we talked about before, about the power of a warm referral. If you show up on dates, and just make your date something that is miserable — where this person has to be right, and if they're not right, on to the next, which is a very common dating trope that people do, because they're trying to maximize "efficiency" (quote, unquote) — what ends up happening is, the people they meet just get this terrible vibe, and they will never care about you again. They're not going to refer you to anyone. They're not going to think about you in the future. They're going to try not to think about you because you basically told them they didn't fit in your box, and therefore, they're useless to you. And what I prefer is a world in which, if you're already putting in the work of trying to source really good people that you'd get along with, then chances are, even if they're not perfect for you, their friends could be or someone that they meet. And so I still always come back to this idea that, no matter who you're meeting and no matter what the context, it's so much healthier to create a world where they want to see you again, where they want to invite you to something, invite you to meet their friends.

SPENCER: Right. They probably have a friend you'd like even if you guys aren't right for each other, which you probably aren't, right?

STEVE: Yeah, you don't have to go back to the app again, and schedule another five dates. You can just ask that person, "Hey, what's going on next week? We don't have to go on another date, but I heard there was a hike getting together." And someone can say, "Well, yeah, come join me and five other single women for this hike." And suddenly, boom, you now have essentially met five people in the span of a single hike rather than having to set up five more drinks dates where you're out 100 bucks each time.

SPENCER: That reminds me of a strategy that you told me about that you use to make dates more fun, in terms of choosing the place you meet carefully. Do you want to just mention that?

STEVE: Yeah. I think this applies to virtually everyone for whether it's even a date or not. I think about all of the things that I would want to do as part of my bucket list in a city, for a trip, or in a given week. I maybe want to spend my Saturday going into the woods. I want to meditate. I want to have some good coffee. I want to do some journaling. For me, that just becomes my date. So whoever I'm dating, it doesn't matter so much who it is, I just want to find the kind of person who's going to resonate with spending a Saturday in this way and, even if we're not super compatible, we can still enjoy the time we shared. I'd still get to check all of these things off my boxes, because I wanted to do those things so it feels very nurturing and cathartic. And then, if this person ends up being really awesome, then maybe we'll want to see each other again. Maybe we'll want to go to another thing together.

SPENCER: But worst case, you did an activity that you wanted to try out anyway.

STEVE: Yeah, worst case, I still had a great Saturday doing every single thing I wanted.

SPENCER: Cool. Okay, the second piece of mathematical dating advice that I sometimes give people — and I want your reaction on — is this idea that we all are looking for somewhat different things when we're dating. But some of these are more common, like, if you want a very stereotypical form of beauty, there's going to be (in some sense) a lot of competition for that. It's very in demand. Whereas, some of the things we're looking for are more idiosyncratic, like, "Oh, I really want to date someone who loves board games," let's say, because I just love playing board games all weekend long. Or maybe there's a type of beauty that you really love that is not as commonly loved. And so this piece of advice is that, if there's some idiosyncratic things that you really, really, really like, and you find that, even with really high levels of those, you continue getting a benefit, optimize very heavily for those in your dating and optimize less heavily for the standards that everyone likes. And by doing so, you'll actually end up with a partner, on average, that's much more compatible to you, because basically, there's way less competition over those idiosyncratic likes. Any thoughts on that?

STEVE: Yeah, I think that bears out in the data, certainly, that people who are more idiosyncratic in their preferences in what they're looking for simply will be able to much more rapidly find the kind of person they're looking for. I think OKCupid has a really good blog post about how men typically message women and vice versa, and it basically showed a curve indicating that, of the people who are rated 0 to 5 stars, women who are rated 5 stars (meaning the most attractive) get (it was something like) 90% of all messages. So if you're only going for people who are generically attractive, frequently you're going to end up with people who are just overwhelmed by low-quality messages. They're less likely to respond, they're more likely to be really annoyed if the conversation doesn't go somewhere meaningful.

SPENCER: Right. There's gonna be a power law where the most conventionally attractive people are going to have dramatically more messages than everyone else, and it's going to be really hard to get through to them, right?

STEVE: Yeah. And the idiosyncrasies are really what makes conversation fun on these dating apps. Because if you imagine, most people right now are in the middle of one of the worst slogs of their life, as it pertains to dating apps. A lot of people are going to apps like Tinder, where they'll match with 20 people in a day. And they'll send the same message to 20 people in a day. And the next day, they send the same message to another 20 people. And it's usually like, "Hey, are you free this weekend? Want to grab a drink?" or, "Hey, you're cute." It's like that all the time, on repeat. And people burn out so quickly from this, because if you're only messaging people or matching with people for whom their only shared characteristic is that they're generically attractive, then what are you actually ending up with? You have nothing to talk to them about. You have no topics of conversation other than your thirst for them. And that's certainly not a topic that the vast majority of women have any desire to talk about — men's desire for them — "Cool story, bro, you and the rest of the people here." So I think being able to instantly begin talking excitedly with someone about any given number of topics that are your pet topics — things that you could nerd out with anyone about for any number of hours — that's something that, for me, makes online dating amazing. It makes it into a place where I can, if I want to talk about Magic: the Gathering right now, I can quickly set my filters so that I'm more likely to find people who will happily nerd out about that. If I want to find people who will show up to a matchmaking event together as a duo just to be able to then nerd out and talk about the experience later — like, "Okay, who did you get? What were the conversations like?"--- if anything, I would love to do that for a date, because that's a way to find the kinds of people who are open-minded, who are open to new experiences, who are able to talk critically about their dating experiences. That, for me, is just an unbelievable sign of compatibility, to be able to have someone who can exist along those same dimensions, who enjoys conversations in those dimensions. And I recommend that to everyone. To boil it down, when I'm giving someone advice (whether a friend or client) for their profile, the way that I try to capture that, is I say, "If you were to remove all your photos, and all you had was a text with a profile, can you write a profile that your friends would read amidst all the other profiles on this app, and instantly identify it as yours?" How much of you can you put into your profile in such a way that your most wonderful and interesting idiosyncrasies are on full display, so that you attract exactly the kind of person who would nerd out about those same idiosyncrasies.

SPENCER: That's great. And actually, that ties in really well to my third piece of dating advice I sometimes give, which is that I think people often want to seem generically attractive, which is what you were talking about before. That means, I think, often trying to hide things about themselves that maybe they feel like are weird or odd or unusual. And it might actually be more successful to double down on those things, to say, "You know what, I am a quirky video game lover," or "I am someone who is obsessed with math," or whatever it is, right? And maybe other people think that's kind of weird, but on the other hand, you're gonna stand out, and maybe you're actually going to be more likely to get a hit with someone who you're super compatible with, than if you try to be generically attractive.

STEVE: Yeah, I think that my experience over the years has taught me — almost to a fault — that people really want the honest story. They want to know who you are. It's not just that they want to see an attractive face on an app. They want to get to know who's this person behind the tech? Who's this person behind the profile? And the fact of the matter is, if you look at me on paper, it could be like, "Oh, I'm some homeless dude who doesn't have a real-people job and just travels around, not knowing where he's going to live, where he's going to eat. He's not looking for a committed relationship." All of those things, if you put that on a dating app, you would think, would make someone say, "Oh my God, avoid like the plague." This is all of the things that make them...I can't even take you out for coffee because I can't afford coffee. That kind of a thing is something that — depending on how you frame the story — certainly, that could be terrible.

SPENCER: And yet, you have had more dates than I think anyone else I've ever met and more partners than just about anyone I've ever met.

STEVE: So it comes down to how do you tell your own story and how do you recognize the ways in which your life and the lives of others can intersect in ways that make everyone better off. There's plenty of people that I've met where they'll literally say, "I just got divorced. The last thing I'm looking for right now is another husband. All I'm looking for is someone who can be legitimately honest with me and be a good mirror for where I am right now." And so that's something where they'll immediately message me saying, like, "Thank you for making it very clear what you're about here, and what you're looking for, and the kinds of people you want to bring into your life. I want to bring those same people into my life. Can we do this together?" Because then it's a team effort, and that's the way I've always framed, on these dating apps, is like, "Let's meet up, not even try to date one another, but to think about, to nerd out about who we actually have found ourselves to be compatible with over the years, and to seek out any of the events or gatherings or refer each other to friends who would make a meaningful difference in our lives." And sometimes we meet up and, within minutes, we're like, "No, we're actually the people for us. We want each other. This is great. We are compatible. Let's pursue this." And then other times we meet up and we're like, "Oh, cool. Definitely not compatible, like you're about to leave the country for the next two years, because you have a new PhD program somewhere. So this is not going to work out on any logistical frame. But let's stay in touch. Let's find out what country you're going to because you're probably going to need friends there. You're probably going to need housing there. You're potentially going to need to find work there." And on all of these dimensions, being able to pool our combined networks and still have that loving attention, is critical. Because all it takes at that point...I can go on a ten-minute date with someone and be able to, six months later, connect them with someone in a new country completely happily and in a way that really moves the needle for them. And I feel like that's something that is so under-recognized, the ability to make a meaningful difference for other people, and not need anything in return, but just to have that mutual possibility space open up on both sides. And you only get that if you treat someone with a sense of genuine care and curiosity for who they'll become in the future.

SPENCER: Yeah, I think that's a wonderful way to look at it. There's so many ways we can help each other that we don't even think about. It's not even on our radar when we're meeting a new person for 20 minutes, like, "Oh, I could help their sister with this. And they could help me with this problem I have," and so on and so forth. One of the things I think is really amazing about you, is you're always looking for those opportunities to help others and so much is created out of that.

STEVE: It's something that was partly by necessity. I can't deny that. For so much of my first several years, just trying to make it through another day, I always would try to find what are the ways in which I can help people that stack, so it's helping me find housing, helping me find income, but also helping every other person go similar paths. So if I went to this particular group, posted there about something, and then it turned out to be really helpful, I can then refer the next ten people there. Each time, I would try to discover this on my own, and then relay that information to as many people as I could and that really, I think that's one of the ways that a lot of communities form — communities of purpose, essentially, or communities of practice — trying to take what it is that you're trying to learn and find other people who want to join you for it. The best example of that is, I don't know if you've seen the CouchSurfing app, where you can just show up in a new country and post to the CouchSurfing app saying like, "Alright, I want to meet people who want to go for this particular hike or go visit this particular monument. Who's down?" And then anyone who happens to be on that app in that country can just say, "Oh, I'm totally down, let's go do it." And then, in meeting those people, you already have a solidified purpose for what you want to do, and the community is already starting to form because you have multiple people who want the same thing. And then if it turns out that you still want to keep exploring, and there's other people in that group you want to follow up the next day, then follow up the next day, see what else is going on. Then it's almost like an emergent community that can form just from a few people sharing what it is that they're genuinely open to. This is how I went to Thailand two years ago and I knew zero people there. And yet by messaging one person on OKCupid, who then invited me into a community gathering that was happening when I arrived, literally just in the first four maybe (two to four hours) of arriving for the first time in the country, I already had a group of about 20 people who I could talk to about anything and ask them about what else should I be doing here. What are some other ways that we can all get to know one another? It can happen so quickly and so (almost) effortlessly, when you approach it with the intent of finding out who are the other people who want to learn or accomplish the same thing.

SPENCER: Last thing I want to ask you about before we finish up, is how do you deal with 'moochers' or people that are not in it to give back, people who are just taking? You must encounter people like this because you're meeting so many people all the time. Do you have a radar for them? Do you avoid them? Do you have a way of interacting with them? What's your thought on that?

STEVE: Yeah. It's kind of funny. I know there's an Adam Grant book called "Give and Take," and it's all about this. It's essentially dichotomizing people, saying there's givers, there's takers, and there's matchers. Givers are just always happy to give in excess. They come up with new and creative ways of giving even more. Then there's takers who just take whatever they can; it's always zero-sum. If there's any opportunity for theft, or graft, or just like "Done, let's take it," they just don't believe that other people are inherently honest or trustworthy, and so for them, it makes rational sense to take whatever they can and then just survive on their own merits. And then matchers are the people in between who try to give but, if you burn them once, they're just like, "Alright, yeah, you've got to pay up again before I'm ever going to trust you again."

SPENCER: It's like tit for tat, like, "I'll help you on the assumption that you'll help me. But then, if later you burn me, then it's over."

STEVE: Yeah, I think there's really good instances of how to detect it in their language. A matcher is someone who's...I get these kinds of business things all the time on LinkedIn, where someone's like, "Hey, let me help you if you help me. I got a proposal for you. You get me these five clients, and I'll give you 20% of each." It's just such a standard thing in the business world, like commissions, things like that, referral bonuses. That's essentially the matcher mantra, it's, 'If you do this, I'll do that.' The giver mantra that I've been trying to work on is much more tied to what it is that we can do together that benefits, not just us, but even more people beyond us. This is an example. I had a friend who arrived in New York a couple years ago, and we were introduced via friends. She arrived, not really knowing what's going on with her life. She wasn't from the US. She was trying to find work before her visa ran out. She was super nervous. And I was busy at the time but my giver instinct came out because I'm like, "Oh, this person probably needs help with finding housing, finding work. And I've been in this position. I get it. So I want to help." And so what I did was call together a bunch of different people. I didn't want to make it just me doing all the giving. On one hand, a friend had offered me his apartment to stay in and he said, "If you need to have other people stay, go for it." So I was able to offer her a place to stay, first of all. Secondly, I had multiple other friends who were looking for work. And so I was able to put her directly in touch with other people looking for work so that their combined efforts could just increase the total surface area of what's available. If you have three people looking for design jobs, then it's 3x the amount of total design jobs that you can have access to because each person is combining the things they're looking for. If you get one rejection, you can still pass it off to the next person with what you learned about why you got rejected. I also brought friends together who were from her country, and introduced them so that they would be able to have (almost like) the emotional support of someone who's been through this kind of crap before, knows what it's like to not be in your country. And on each frontier, by virtue of not just thinking about what this person needs right now, but thinking about what else can this person, just by her own existence, be able to provide to all the other people around her, she was able to not just find a job, but also be able to make multiple different friends and maintain those friendships for (now) over a year. And for me to be able to start from a position of, I could have just said no to that initial friend intro, but instead, I thought about it from a position of giving and it turned into easily a dozen new friendships, new types of experiences. The same woman had invited me then to multiple other events and communities that she discovered in the process of her growth, trying to find work, find community in a new city. The spillover effects of a good process of giving, they basically never end because this can go on for years still. She referred me to this really cool prize, the David Prize in New York, that I thought would be a's basically grants given out to people who are trying to make big changes in a city. Just so much that comes from that one instance of giving.

SPENCER: There are just so many ways any person can help another person, if they really can figure them all out. A lot of times, we just don't even realize all these different possibilities.

STEVE: Yeah. And then I guess the taking mindset is another one that...

SPENCER: Yeah, how do you avoid that?

STEVE: How do you avoid it? For me, it is so easy to spot in someone's lexicon. It starts with someone I don't know that well saying, "Steve, I need you to do this for me." That's the first line. I'm like, "Oh, okay. Okay, what's gonna happen here?" It's not even checking in, like, "Steve, how are you? What's going on in your life?" or "Is this a good time for you?"

SPENCER: So how do you handle it, when someone does that?

STEVE: There are two things that happen at once. There's like how I'm internally processing it, and how I'm categorizing this person in my own mind, but there's also how I choose to respond. So internally, I'm like, "Oh, this might be someone who is not particularly thoughtful." They may be at a place in their life where they're just resource-constrained and attentionally-constrained, and so they're not being able to add a lot of spaciousness to the way they talk to people and it comes off as very...gross.

SPENCER: So like a temporary taker due to [the fact that] they're in a stressful or difficult situation.

STEVE: Yeah. I check up on that and I hold that as a possibility, because I don't want to write someone off before I get to know what their actual situation is. I have been there for people who were in a very 'taker-y' mindset, because a lot of crap just happened to them in a row, and they were not prepared to have to deal with that, and they were terrified of making asks, and they could potentially be crying on their end as they're typing this because they're just really scared and frustrated. That's one element. It's like a yellow light. I'm already thinking, "Okay, there's a challenge here. I might not want to go forward with this, depending on what the ask is." If it's a relatively easy task, and I can do it in under five minutes, typically, I'll still go ahead with it. Even if it's a taker, I still want them to have had a good experience of engaging with me, because that's part of my own value set in the world. I want people to have good experiences with me, even if they're not necessarily operating in the best faith.

SPENCER: But how do you prevent them from taking advantage of you, because aren't they going to ask again?

STEVE: That's the next step. If I have already given them the yellow light, essentially, I will then follow up with a, "Hey, I want to talk about what just happened and how you made that ask because it made me feel really uncomfortable for the following reasons." And then I'll explain point by point why what they did didn't feel like it was done in good faith, why (by virtue of them doing that) I am far less likely to trust that I can refer them to the next person because they may treat the next person in that same way. And the worst thing for me is when someone comes back after I have made a referral and said, "Who the hell was that person? They were terrible. They treated me with no respect or dignity." I never want to have that happen. And I've learned very quickly from the times in which that did happen, that proper vetting is very important. And the vetting starts — if it's online dating — it starts at the level of looking at someone's photos and profile and how they message you. If it's LinkedIn, it's literally the way they first connect. There's a lot of people on Facebook now. I don't know if you've seen those Bitcoin/blockchain/forex trader people who will relentlessly just go into people's social networks and try to co-op their attention and get them to participate in random Bitcoin scams. They always start off by just cold friend request, no message. And maybe they'll say, "Hey," And then I'm like, "Okay, you messaged me on Facebook, not being my friend, with no mutual friends. What's going on here?" I'm already on high alert. And then I say, "Well, what's your deal? What do you do? How did you find me?" And then they'll be like, "Hi." This happens routinely, where all my red flags are already happening. They're not conveying information. And I'll say, "Well, what do you want?" And they're like, "Well, that's not a very nice way to greet someone." I'm like, "Okay, you're still not giving me an answer. What are you here for?" There's a certain evasiveness. There's a miserliness of words of someone not actually conveying their genuine intentions in a meaningful way, not doing any of the work to make sure that I have a good experience of engaging with them. And so anytime I notice that, I try to call it out very quickly.

SPENCER: But what about a really savvy taker who's going to do the "Oh, it's so good to talk to you. How have you been?" but, really, it's all about getting what they want.

STEVE: That happens, too. Sometimes savvy takers can still be essentially useful in a way, because they can be doing something that's really...I think of maybe like a Steve Jobs type. He's someone who seems like he's pretty willing (at least when he was alive), to do what needs to get done to make a product move forward. And so he may be a taker, he may be thinking about this from an anti-competitive standpoint. But if what he's working on is actually something that I believe in, then I might say, some people just happen to have personality traits that make them very good at getting a certain thing done, but not very good at other things.

SPENCER: He's very oriented on like, "I must make this thing succeed. And I'm going to need to rally other people to do it. But it's not about what I can do for that, and it's really about how it can help my project."

STEVE: That'll completely change who I refer them to. I think that's the biggest thing I'll note is, how much attention I give them and who I refer them to. Those are the two biggest things that shift when I encounter a taker.

SPENCER: So who would you introduce them to and who wouldn't you introduce them to?

STEVE: I've definitely met plenty of takers in the dating industry, people who are running their own app, and they'll start off by saying, "Steve, I want to get some PR for my app, so can you give me some?" And I'll be like, "Okay, okay. Well, let's find out. Is this an app that is deserving of my attention? Is it an app where, if I actually did get some good PR, if you built a really good product, then I will forgive you any of the personality flaws that led to me having a crappy experience with you in our chat."

SPENCER: Because it's something you want to exist in the world, right?

STEVE: Yeah. And my friends will actually like this. This is a good thing for the world to have, so I'm going to go out of my way to help, even if I don't necessarily like the person that I'm helping. What I won't do though, is introduce that person to a friend of mine who's a strong empath, who is not looking for that kind of energy in their life, or might be more susceptible to someone taking from them. And if I do make an intro to someone, I will almost always caveat it with, "Hey, I'm making this intro for this very specific purpose. I want you to talk to this person as a reporter in the industry, not as a friend. I'm not saying you shouldn't be friends with them. But I'm saying that I don't currently feel comfortable making a good faith referral of this person on friendship grounds. But I do like the product." I'm very specific and I try to account for as much of the variation in someone's experience as I can when I'm sending that message.

SPENCER: Well, what if the person is really selfishly motivated? So it's a taker; they're not building an amazing product that's going to make people's lives better, it's more just selfishly motivated. Would you do that?

STEVE: This has happened before, too. I've had serial grifters show up in my networks. Sometimes they'll be introduced via a friend who might be more trusting than I am. While I'm trusting, I'm also a checker. Maybe I can personally withstand trusting someone, but I'm not going to bring that into my network and force others to deal with it, if it's something that could be very toxic for them. In those cases, I will literally go to our mutual friends and say to them, "Why are you friends with this person? Here is a litany of the things that they've done that caused me to lose faith in them. And given that you're friends with them, you're implicitly giving a boost to their social credibility. So I want to understand from your perspective, what is at odds? What experiences have you had that should potentially change my view? But currently, here's my experiences that explain why my view is currently the way it is."

SPENCER: So then, either you're gonna get evidence that, "Oh, this person is actually a pretty good person, and maybe I just had a weird experience with them." Or it's actually going to reinforce your view that this is actually a taker who is kind of leeching off of the network, and then maybe you're gonna create more common knowledge about that fact. Is that right?

STEVE: Yeah, absolutely. And like I said before, I want to respect that people might be temporary takers. For instance, I had a friend recently say to me that a woman he met who we knew, was a little bit standoffish, and much more hostile than he had expected, or than I had led him to believe she would be. And it turned out that she had just been sexually assaulted that same week before meeting, and was just absolutely not ready to deal with another person, even someone approaching her with kindness. She was still in a very fragile state, and it was probably not the right time to have any intro made. You can't always account for the minute and minute-to-minute variations in someone's character. But what you can do is try to orient yourself and your network toward encouraging growth whenever you can, toward communicating about the things that you find either problematic or worrisome so that your friends can be prepared for what's to come, and also for just calling people out when they have bad behavior. I like to do it personally. I generally try not to make it a public thing, where you just have a lot of people with no context and a lot of defensiveness. I try to go as directly as I can, and I try to come from a place of empathy and from a place of like, "Hey, in the interest of all the interconnections we have, in the interest of still getting to know you better over time, I just want to bring up something that's been sitting really poorly with me, and have us be able to talk through it." They don't have to, but I find that it's just — someone did that to me recently and it was — totally transformative, where someone came up to me on Facebook a couple of months ago, and I guess when we first met nearly 10 years ago, I had said some things that she found very off-putting at the time, and she didn't really bring it up for years, and then she finally confronted me about it. This was now almost a decade later, saying like, "Hey, this is what you had said before. I still feel weird about it. Do you still feel this way? I just want to bring that up because I still feel uncomfortable because of this." And I thanked her so much because basically at the time, I didn't realize that she was being impacted in that way by what I was saying. I was making a comment about experiences in the dating industry and she had happened to have some pretty negative ones and strong opinions about it. I was speaking too cavalierly at the time and it just made her feel really uncomfortable. I was just so grateful that she was willing to come and tell me that because it helps me reflect back on how I could have spoken more judiciously, how I could have been a better person. Essentially, for someone like her who had just arrived in the city and was trying to make new friends, to hear such rough talk about dating apps and people's experiences on them just made her feel really uncomfortable right off the bat. I just loved that she came to me directly and said, "Hey, this didn't sit well with me." It's a form of restorative justice that I truly believe in and stand by, the ability to call people out, call people in, and help make it so that you can co-exist in the world a little more easily because you've cleared the air.

SPENCER: Steve, this was super interesting. Thanks so much for coming on today.

STEVE: Absolutely. Thank you, Spencer. I love when you insert any degree of additional math and logic into the things that I'm otherwise [laughs] thinking about or working through, because (oh, man) there's just so much of it. And I like that you bring your perspective to flesh it out even further and make it so that people can think a little bit more judiciously about how they approach any given life scenario.

SPENCER: Where can people learn more about your work? If they want to hire you as a dating coach for themselves or for their friends or for their family members, how would they do that?

STEVE: The easiest place to find me is just through my website, And I also have the dateworking podcasts, and I have a second season coming out pretty shortly. I think we've been recording around the same time, so I'm really excited about that as well. I've been focused a lot on what's going on with the pandemic, how it's shifting, how we find dates, how we find roommates, how we find new jobs when 30 more million people are looking for the same jobs. So yeah, the dateworking podcast, And you can find me on any social media platform at Steven M. Dean, like Instagram, Twitter, Facebook.

SPENCER: He means any platform. [laughs]

STEVE: Any of easily 400+ platforms.

SPENCER: Oh my gosh, okay. Thanks so much, Steve.

STEVE: Thank you, Spencer.





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