When online dating isn't working out for him, Tristan Attwood decides to analyze the data himself.

Tristan Attwood works as a business analyst for the airline industry. Originally from the Portland, Oregon, area, Tristan relocated to DC more than a decade ago after serving as a field organizer for a Senate campaign. Having been "unschooled" as a child, Tristan attended Linfield College in Oregon in the early 2000s but did not technically receive a high school diploma until getting his GED from the District of Columbia in 2015. He spends his free time renovating his DC townhouse, playing dungeons and dragons, and apologizing for the airline industry. He resides in DC with his wife, Jessica, and newborn baby Roland Tiberius.

This story originally aired on December 20, 2019 in an episode titled “Dating by the Numbers.”

Story Transcript

So I was sitting around. I was hanging out. I was checking my phone, like you do, and I realized that 80% of all the photos in my phone were of my cat Peek, which is adorable but a little weird. And then I went and texted my friend about this and I realized 80% of my texts to my friend were also about my cat Peek, which is still adorable but like a little weirder.

And I realized I should really expand my social circle. I should really get out there, meet some new people, so I decided I should start dating. I was single at the time.

But the last time I went out there and I was trying to meet people, trying to date, it was in college. It was in undergrad, which is a very different environment from being a professional in D.C., right? It’s much easier. So because I wasn’t into the bar scene, I decided I’m going to use the internet for this. I’m going to use OkCupid.

And the reason I used OkCupid was because it is, or it claims to be, a data-driven dating website. They've got a whole data blog. Create an account there, answer a bunch of questions, they use some algorithms to match with people. As a data guy, I really liked that. I really loved that kind of rigor to it. I thought that’s going to make things better.

So I get up there, I create a profile, answer some questions, start matching with people and I go on some dates. Nothing is really happening but it’s fun. I’m getting out there, I’m meeting new people, I’m not taking pictures of my cat. It’s good.

Then I get matched with this girl. She's cute. And, according to the site, we are 99% compatible. We are basically perfect. I’m thinking, “This is awesome. The science has just delivered my soul mate to me. I can check the box on dating. Everything is good. Just solve this right here.”

So we go on a date. We get drinks, just chatting. You know, normal first-date stuff. Until, apropos of nothing, she just suddenly says, “You know, I don't really believe in rape,” which is not how I expected that conversation to go.

And I didn’t really know how to respond, because like how do you respond to that out of nowhere? So I just sort of said, “Oh?” And did whatever.

Over the course of the conversation, it became clear that she was of the opinion that you could always fight someone off, which is not something I believe. I was trying not to engage but like I sort of couldn’t help myself because that was weird. so I’m like, “Okay, but like size and leverage and all these things.”

And she says, “No, no, no. That’s fine. I've got a combat knife in my purse and I've taken classes on how to use it,” which is really not how I expected that conversation to go.

So I took a quick look, make sure I know where the exits are in case I needed to run. Date ends uneventfully compared to that. We say our goodbyes. I give her a fake phone number. I go home.

And I fell into this really deep weird funk because the data, the science had told me, “Hey, we are 99% compatible.” It’s like 1% off from perfect. It’s basically perfect. And what does that mean that this is what perfect for me looks like? Right. You see my problem.

So I got way inside my head about that for a couple of days. And then I found myself just staring at my profile on the website, which is always a healthy thing to do. I’m staring at it, I’m thinking, “You know what? No. Their data got me into this mess. My data will get me out of this mess.”

So I created a spreadsheet which is, again, always healthy. I created a spreadsheet and I just started recording basic demographic information. So name, age, what do they do? How did I think the date went? What did I think of them? Did they talk about having a knife? Basic information.

And I start going on dates and I’m just looking for anything that pops up. I don't really know what’s important so I’m just looking at anything. And I found something, which was interesting. So, for women in the age range I was dating, according to the US Social Security Administration, the most common name is Jessica. So about a third of all women, roughly, born between ‘80 and ‘89 are named Jessica.

But when I looked at my data, 40% of all the women were named Catherine or some version of Catherine. So Catherine, Kate, Katie, Kat, whatever. Some version of Catherine. Which is doubly interesting because they were only screen names. I didn’t know that her name was Catherine before I went on this date with her, but it was because they were all named Catherine.

And this was awesome, right? This validated my approach. I’m like, “Okay. I am clearly dating some interesting subset of the population.” I know, right? “And I can use this. Like I can make things better using this leverage I have, this data.”

But knowing that my next date is probably going to be named Catherine is interesting but not useful, so I need to find out what the useful stuff is. At this point, I switched from a spreadsheet to a database I made in SQL one day. Still super healthy. And I was collecting all the same old data but I was also collecting a bunch more data.

So ethnicity, religion. Is religion important to them? Where did they go to school? What’s their degree in? A whole bunch of things. About 20 fields all told. And I thought, “This is going to really help me optimize this, help me fix this.”

I’m going to stop here for a second. When you create a database that has 20-something data elements in on it and then you go on your first date, you're not a good date. So in a first date, ideally you have like lively, interesting conversation. I was just mentally going like, “Data element one: Name, Data element two: Age,” and just going down the list. Which is, a) not how people talk and, b) made me seem like a crazy person, made me seem like a stalker which is definitely not what I wanted.

Luckily, I was able to realize I was doing this. I was able to be cool for once, which was a great surprise. And then I was able to move on.

So over the course of dating, over the course of about two years, I went on give or take 250 first dates, which is too many first dates. Like that is too many. But what that did do is that gave me a ton of data. I could really run some analysis on this and create a profile of someone I matched well with and someone I didn’t, which was awesome. Because when you go on 250-something dates, you get so dejected, right? Because most first dates are not interesting. There's no sudden knife. It’s just boring, lifeless conversation. And that really drains you emotionally.

So I must have told my friends I’m giving up dating a half dozen times, which they loved, by the way. They loved that. But with this profile, I was able to actually be really strategic about my emotional energy, with the kind of work I did. So if I matched with someone and nothing is... there's just red flags, great. Move on. If I matched with someone and it’s all great, okay. Perfect. I can put my energy into that.

So what I was finding was my kind of mathematically ideal date was ethnically Jewish, but religion was not a big part of her life. She went to a small private college. Interesting side note, if they went to an Ivy League, huge red flag. Huge red flag. Never would have guessed that but if you went to an Ivy League school and went on a date with me, just terrible, boring conversation. You’ll want to leave. They had a very dark sense of humor and the most correlated with things going well was them messaging me first, which was interesting and probably said some stuff about me.

So all of this was great when Jessica messaged me first. Great sign. Turns out she had a master’s degree, another great flag. She went to a small private college.

So we go on a date, things are going really well, I’m getting excited. I’m thinking she's awesome but I wish she would match a couple more things, which she did on our second date when dark sense of a humor is a good flag for me and she made so many murder jokes. It was just nonstop murder jokes, which worked for me to the point where, about a year, two years after that, we got married. And then about three months ago we had our son Roland who’s tying in perfect.

But here’s the kicker. So I went on 250 first dates, built a database, did all this analysis, found Jessica. Right? Great. Perfect. Except that Jessica went on one date with me and was done. So data and science will get you a long way but it’s not the only way to get there. Thank you.