Here's what 12 years on OkCupid taught one man about finding love

Before Jason Hill tied the knot, he was the preeminent OKCupid user. The Brooklynite recently married a woman he met IRL—but for over a decade he used the online dating site to find eligible women. All told, Hill spent a whopping 12 years on the site, which he believes makes him its longest continual user.

It’s clear that Jason has some sort of superhuman dating stamina—as anyone who’s spent five minutes on a dating app knows, the emotional rigor, confidence, and chill required to put yourself out there is both mentally and physically exhausting. And despite his marital status, Hill’s OkCupid profile lives on to this day—he and his wife use the site to seek new partners for threesomes. I needed to know: How on earth could a person date online for a dozen grueling years? And what wisdom could this veteran dater impart?

I learned about Jason’s story because he is both an old friend and my boss at the startup where we work. If he weren’t my boss, I’d describe the 37-year-old as gentlemanly and kind and a little bit raffish. Tall and thin, he juggles a sardonic streak and a Don Quixote-vibe. I bet he gives good date.

About being the longest running user? Jason learned about this distinction back in 2009, when he attended a meetup of the site’s users and OkCupid founder Sam Yagan happened to show up. When Yagan heard that Jason joined in March 2004, he commented, “That was less than a month after we started.” Yagan was astounded, Jason says, and told him, “You must be our longest user!” (I reached out to OkCupid for official confirmation, but a representative said she was unable to confirm at this time.)

Whether or not he’s the true reigning king of OKCupid, there’s no doubt Jason has seen it all. I recently sat down with him to see just what fuels this dating machine.

MD: You joined OkCupid before online dating was as popular—and accepted—as it is today. What initially led you to decide, Hmm, I’m going to try to date from an online pool?

JH: Part of it had to do with the fact that I had moved cross-country from California to Annapolis, Maryland for grad school, where I was getting my Master’s in Liberal Arts, and my dating options were limited. At 25, I was on the very young end of the students in my program. There were a lot of mid-career professionals—and there were only 50 of us, total. I was trying to reach outside of Annapolis. And I succeeded in finding people online in Baltimore or Washington, D.C.—in fact, OkCupid is how I ended up dating a woman who lived in College Park, Maryland.

Back then, did you go on date dates with the people you met online? That sounds like a nice, quaint kind of a way to meet someone compared to today’s so-called “hookup culture.”

I’m sure that hookup culture was happening —I just wasn’t a party to it. I wasn’t socially adept enough for it. The great thing about online dating for me was that a person clearly indicated interest. And once the person indicated interest, I knew the rules, right? At that point, dating became something I could do easily. Being in a bar or at a party, I didn’t know how to receive or perceive interest and was never able to strike up a conversation or otherwise approach somebody. Whether you call it self-esteem issues, or whatever, it just never worked for me.

What were OkCupid profiles like in those early days?

One of the things they used to have—and I can see why they did away with them, because on some level they were a little creepy—were these “testimonials.” You would literally give testimonials for your friends and/or someone nice you had gone on a date with but who just wasn’t right for you. I had a certain affection for the testimonials, because I had managed to garner a number of very nice ones. I give a good first date.

Otherwise, I would say the profiles then weren’t totally different than they are now.

How do you think your gender impacted your experience in those early days? Today, when you’re a woman on Tinder, and you get a ton of messages that are just, “Heyyy sexy”…

I don’t want to theorize too much about what a woman goes through. I feel my profile was somewhere in the weird gray space between being interesting but approachable. From the time I signed up, I was looking for a serious relationship. I also wasn’t sending those creepy messages, you know? The messages I would send would try for a mix of approachable and forthright, charming and snarky. I will say that I went on dates with a lot of women who said it was their first internet date ever. And that was—

Wait, so you not only went on a lot of first online dates yourself, but a lot of first online dates for the woman?

I mean, hundreds. I’d be their first blind internet date ever, and that became wearisome, eventually. Because there would always be a certain moment in the date where it would get meta, if the date wasn’t necessarily going very well. Two-thirds of the way through a mediocre date you start talking about the process of online dating, which was still a novelty at that point.

It was frustrating because I was ready for a serious relationship, whereas these were often women who had just broken up, were in the middle of divorcing, or were separated and on their first online date. I was like, “Okay, where are the people ready for a real relationship?”

You learn so much from meeting someone in person—it can be difficult trying to assess your attraction to someone based on a photo. What did you learn about first impressions over the years?

A photograph can tell you a lot, but there’s so much more you learn from watching a person move. This is going to sound horrible, but I remember meeting a girl I’d connected with on OkCupid and knowing instantly it wasn’t going to work out.

The date texted me to say that she was getting out of her cab near the bar where we were meeting. I went outside and I saw her getting out, and this was in the dark. The way that she moved from a block and a half away—I already knew it was over. I mean, I had no interest, just from the way that she moved.

There was part of me that was thinking, “Okay, Jason, don’t jump to conclusions, let’s sit down, let’s give this an hour.” About an hour into it, she asked a question and unfortunately, inadvertently, I let out this huge yawn. I said to her, “I‘m so sorry. That was really inappropriate.” It was time for the date to be over, but it turned out my first instinct was correct. Whoever she was, her physicality expressed it, and I could read that physicality from a great distance. We may be able to have a conversation for an hour, but we weren’t going to go on a second date, and I knew that without speaking to her.

So having said all of this, you and your wife did not meet online. How do you think your hundreds of dates prepared you for “the one?”

That’s right, we met through a mutual friend. I didn’t meet the friend online, either. We lived in the same neighborhood, worked in the same building, and rode the same train to work every morning. My friend invited my now-wife over for dinner with me.

The first time I saw her, I opened the door and was just thunderstruck. By the end of dinner, we had hit it off and I asked her out. The first date, we went to dinner, but everything went wrong. She was 40 minutes late, the restaurant we wanted to go to was closed. The place we ended up at was really buttoned up, very boring food. Bad. After we ate, we adjourned next door to a bar I liked, and finally in a much more relaxed setting, I saw her again—that person that I had seen at the dinner a few nights before.

Thanks to all those hundreds of dates I had gone on, what I realized is: At some point you just need to say what you want, especially at the beginning of a relationship, maybe even on a first date. There’s no point in beating around the bush. I said to her that night, “There are three things that I want in a partnership: children, dancing, and threesomes.” She thought about that for a moment and she said, “Okay.”

A few minutes later—we’re sitting out on a patio, and it started to storm. Everybody else ran inside, but we ran under some solar panels. There was no one else around. I said, “There’s some story about kissing in the rain in New York, first kisses in the rain in New York.” She gave me the nod, and then there we were: making out in the rain, in New York City, and that was the beginning.

This interview has been lightly edited for length and clarity.

Mary Duffy’s work has appeared in Pacific Standard and The Scofield. She’s writing a book about her family and Jewish-American culture.