worldbuilding

+ Interview with someone who goes on *a lot* of dates

David Hockney, Mount Fuji and Flowers, 1972

Housekeeping: if you’re interested in being part of my matchmaking database, fill out this form here! Being part of the database just means I’ll contact you about a potential match if you seem like a good fit for someone :) This is free and purely if you’re open to potentially meeting new people!!

Getting into matchmaking feels like falling in love or the onset of a particularly nasty cold. Overnight I’ve become an obsessive, taking calls, looking through my notes, texting friends, struggling to sleep at night. I know, it’s dramatic. I’m dramatic. All of a sudden I’m using words like vocation.

I was panicking last night (I’ve gone through the full cycle of emotions from elation to despair already), like what if I’m not good at this, and V came by and gave me the best pep talk in the world. He said, You’re giving people the most valuable gift of their lives, and they will thank you on their deathbed. Also the worst case scenario is that you’re a 99th percentile matchmaker. I’m not sure if that’s true, but it’s what I needed to hear.

I do have a few things going for me. For one, I’ve been writing on Substack for years and I’ve been doing matchmaking at scale for months, so I literally have a database of cool people. But also I’ve been thinking about nothing other than people and their personalities and neuroses and hangups and passions for the past decade. Another way to put it: for some years now I’ve been a professional romantic, and being a matchmaker is just being a professional romantic in a new way. My intuition is going wild, like I can sort of just tell this is going to turn into relationship coaching, which—how do I even feel about that? I’m wondering if this is how my friends feel about LLM architecture or their SaaS startups, like you can see everything sprawled out before you in the fullness of time. Like: it hasn’t happened yet, but it will.

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People have always sought me out during crises. Breakups, infatuation, heartbreak, career changes, stuckness, loss of faith: that’s when people find me. I think that I attract vulnerability because I am vulnerable. And it’s not my writing, like the truth is that I don’t say anything particularly vulnerable or act very vulnerable, I’m actually compulsively secretive and insular. But I’m vulnerable because I’m sensitive and obsessive and easily hurt. I would get attached to a tree if I made eye contact with it for too long. I always want to fix people.

It took me a long time to learn that I can be ambivalent about these qualities in my personal life, but they’re highly useful in my professional life. I guess that’s just how it works. One of my friends never stops moving, metaphorically and literally. Sometimes it makes me feel crazy: why can’t you just sit there for 45 minutes? But his propensity towards motion is what makes him good. The way I obsessively think about people makes me feel insane sometimes, but it’s also what makes me good.

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Substack feels like a job that I just invented. Matchmaking, even more so. To be clear, I did not invent either, but I stumbled into them with little prior context. I don’t know what the rules are, and often I’m making them up as I go along.

On Monday, I threw a Valentine’s Day themed party for subscribers and friends at Green Apple Books on the Park. It was so fun and magical (thank you, Kar, for letting us have the party there!). I was so nervous the day of as I picked up my snack platter and got balloons and cupcakes and wine. Even though I threw a lot of parties last year (by my standards, at least!) I still get paralyzingly anxious right before. But once I arrived and took in the space, I felt so lucky: how cool is it to get to host a matchmaking party in a bookstore you love? I’m sure no one is surprised that one of my favorite movies is You’ve Got Mail. Everyone purchased at least one book, which made me so happy.

I think that San Francisco is a place that encourages you to be grandiose, and that’s never been particularly me. Historically, I’ve liked my dreams pragmatic and contained. But in the past year I’ve felt like I’m learning to do some worldbuilding of my own, one step at a time.

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Interview with a guy who goes on a lot of dates

For context, this interview was inspired by this tweet:

It made me think that we hear about people who are incels, or who have never been in a romantic relationship at a more advanced age, but we rarely hear about the other end of the spectrum: people who are going on 3 dates a month. So I talked to a female reader who goes on a lot of dates and then a guy, my friend L. This interview is with L and attempts to explore his psyche:

AVA: Okay, so we’re here with L, my friend of multiple years, and we’re going to get some insight on his period of manic dating. Tell me about it. Like, what was the period of your life that you were really actively going on multiple dates?

L: It was right after COVID. I had an injury so I wasn't working as much, I was in New York on medical leave with nothing to do. So I thought, why don’t I just go on dates and hang out with people.

A: When we say a lot of dates, how many dates are we talking?

L: Four, five? Maybe four is an average week?

A: What are these? Dinner dates, drink dates?

L: Probably like, three dinner dates. And like, if I knew them already, they could, like, they would have come over and cook and have a glass of wine.

A: And you were meeting people primarily on apps?

L: Mostly Hinge. It was first spring of New York City post-Covid, 2022

A: Okay. And how was it? Did you like it?

L: A lot of it was the fact that, because I was not working as much and it was post COVID, there was just so much like energy in the air to go socialize. In the beginning it was very fun, but at some point it kind of just felt very draining. In March, my doorman said to me, “L, you are out on these streets.” And I thought, what's happening? Like, what am I doing with life?

A: Okay, let’s presume four dates a week. That's 16 a month. What percentage of people are you asking on second dates? Like, what's the conversion.

L: Pretty high, like, 70% become second dates. I only swipe right on like three people a day, only if I’m really attracted to them, and if we match I’ll text them a lot, enough to know that they can already kind of hang.

A: Okay, one thing that we need to mention about L is that L’s very comfortable texting, which is, like, very important, because if don't like texting, getting dates via apps can feel super exhausting. But for you, you put a lot of work into texting them first. And you generally love texting, I know that about you.

L: I mean, yes. I tweet 70 times a day. I’m comfortable with texting.

A: So I think a lot of guys are gonna be like, Oh my gosh. Like, what are you doing right? Like, why do you feel like girls swipe right on you? A mutual friend recently described you as a “swagged out man,” for the record.