I’m unusually good at meeting friends and potential romantic partners. For a long time, I was actually much better at beginning relationships than maintaining them—I’m lucky to have dated a bunch of cool people and screwed up all of those relationships before meeting my wife, the coolest person of all.

Also, I notice that I know lots of dateable single people, for whom meeting people seems to be the bottleneck. They’re very much relationship-ready but can't seem to place humans into life. One eminently dateable friend asked me how I do it, so I am here sharing my opinions about how you can meet potential partners, besides just being extroverted to the greatest extent you possibly can.

You will notice that this advice is basically targeted at heteros. I’m aware that there are lots of queer-specific dating spaces/contexts/etiquettes that I don’t know anything about, so if you’re not a hetero, some of this probably applies but maybe not all of it? But you are a better judge of that than I am.

Search Space

Someone you want to be with probably isn’t in your immediate social group, for a couple of reasons. The obvious one is that if they were, you’d be dating them already. The less obvious one is—

Thesis: Similarity is compatibility, and a good relationship is smooth

Antithesis: Polarity is attractive, opposites are intriguing

Synthesis: You want enough similarity to be able to communicate across the interesting distances

This implies an area of search. Find spaces where you understand the culture somewhat, but where you’re not strictly of it. Then, extrovert in those spaces. For me, this would be: crypto stuff, startup-related spaces, perfume boutiques, fine wine consumption areas, and a few others. In any of these contexts, on a global scale, I’m in the 99th percentile of cultural similarity to many of the people there, but probably not in the 99.9th.

These spaces are not all the same, and they will present advantages and disadvantages. It’ll be easier to socialize in places that are more socially carefree—like, a wine industry night with a lot of drunk Europeans will probably be much less awkward than, I don’t know, a Medieval Studies conference. However, in more awkward spaces, being more daringly extroverted, if you can pull it off, will be disproportionately effective. It’s really easy to be the most approachable person in nerdy, bookish milieus.

Also, obviously, gender balance is a factor to keep in mind. Anything vegan or health-related or fitness-related is going to be really female-skewed unless it’s health-related in a Joe Rogan-y way. Pottery classes lean hard non-male and are fun. In the other direction, you’d be surprised at how many guys at jiu-jitsu academies are high-earning smart people in good shape.

You get in these spaces by inviting yourself. If you have cool acquaintances in different social scenes, you will not die if you send them a message saying, “Hey, I want to leave my house more, are there any cool events you’re going to soon?” This is easier if you’re befriending lots of people, which you should already be doing.

Speaking of which.

De-Emphasize Dating Sites and Other Dating-Focused Places

I hold it as self-evident that most people are at their most charming when they aren’t manicuring their personality in one or another way. You are cutest and most interesting when you’re being yourself. This is impossible to do on a dating site or at a dating event; by default, you are formatted into a certain shape. (Also, being a man on a dating site is difficult for gender-specific reasons.) That’s not to say that doing these is a bad idea—it can work—it’s just, IMO, not the best, unless your requirements are extremely specific, like, you need someone who’s into esoteric Japanese rope bondage, or whatever. (And even then, there’s probably a real-life event you can go to, in any major city someone is getting up to freaky shit somewhere.)

BUT THEN HOW DO YOU ENSURE THAT THE PEOPLE YOU’RE MEETING ARE SINGLE??? You do not. Try to consider meeting a partner a side-effect of having an active social life. If you’re meeting lots of cool people and having fun with them, that is Simply Good. Some proportion of them will be single, and some of them will be partnered people with single friends. You just will meet potential matches if there are enough human beings flowing in and out of your life, and you’re having fun conversations with them. If you’re in doubt, “um, hey, are you seeing anybody,” is a flattering question to ask someone you’ve established some degree of rapport with, and nobody you want to date will be a jerk about it if the answer is “yes.”

If this sounds tiresome, and you’re only interested in meeting people you could have sex with, you might not be in a healthy state of mind. Being open to life and being open to what the world could give you on all fronts is where you want to be, and it’s also the most attractive energy you can emanate.

Meeting Strangers

Most people on earth you can date are strangers. Therefore, if you can do it without incurring too much damage, you should talk to strangers. QED.

From a female perspective, on the topic of meeting strangers, men will basically never mind if you strike up a conversation with them. Never! Do whatever you want! From a male perspective, on the topic of meeting strangers, you usually hear two extreme positions. One is that it is an archaic practice engaged in only by pickup artists and scoundrels. The other position—frequently voiced by pickup artists—is that you should basically approach attractive women whenever possible, and develop a detailed routine for doing so.

In my experience, the truth is somewhere in the middle. On the one hand, I’ve had a couple of meaningful relationships begin with conversations with strangers. On the other hand, I agree that if you don’t do it right, you can make people really uncomfortable.

So here’s the actual thing you do. Try to start a conversation with anyone who intuitively seems like a friend or partner. (Do this on all genders, this is a general life skill that’s incredibly valuable and can be honed constantly.) The moment you get a sign of non-interest, bail out. The thing I liked to do was say, “hi, my name is Sasha,” at which point I would cancel the interaction immediately if I heard something like, “uh, hi,” instead of, “hi, my name is [another name].” Just don’t do this in any location where you’re the only two people and there are no comfortable outs—like, say, if you’re in an elevator, or alone on an empty street. Basically, if there’s any probability that you will be spooky due to context, don’t even think about it!!

Anyway, at that point, you have a low-pressure conversation, that then might naturally flow into the question of “hey do you want to go eat some food sometime,” or not, depending on how nice the conversation is. Keep it ultra-casual. The best frame to have is that this is a Normal Interaction, not a Romance Interaction.

In terms of the intuitions, a little bit of context gives you more information about a person than you’d expect. (This is where search spaces re-enter the equation.) For example, one of the people I started a relationship with was sitting at a non-mainstream wine bar, reading a book, at a weird time. This actually tells you a lot: the person probably has a non-conventional life path, is an epicurean, and reads paper books. For me, those three bits indicate that I’m more culturally similar to that person than 99% of people on earth. The other example was a librarian I saw a lot at the library I frequented in school; she had an unusual sense of style, was slightly quirky conversationally, and, well, she worked at a university library. Again, 99%.

Being more of a flaneur is the best way to maximize this kind of interaction. Always be reconnoitering. Remember the wise words of Kurt Vonnegut: “I tell you, we are here on Earth to fart around, and don't let anybody tell you different.”

But What About That Whole Thing About How You Find the Person You’re Looking For When You Least Expect It

Thesis: lots of people seem to have the experience where they find their partner when they least expect it, and

Antithesis: if you’re not trying to meet people, how do you meet people

Synthesis: if you’re super lonely and approaching the world from a dating-first perspective, you will be the least attractive version of yourself in the most crowded, worst markets, but if you increase the amount of human possibility flowing through your life in a more intelligent way, good things will happen to you

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