Date Lab has been playing matchmaker for eight years now, but moms have been doing it for centuries. So when we wanted to choose someone to send out with Tyler — a gregarious, charming poetry grad student who describes his dream girl as “indefatigably curious” and “socially dynamic” — we decided to leave the decision to his mother.
Tyler: It seemed a win-win scenario: If the date goes well, I’m very happy. ... [If not], I could give her crap about it for the rest of our lives.
Fay, Tyler’s mom: I thought it was a clever idea. I’ve never fixed him up with anybody. I read through all four [of the applications Date Lab provided] with an open mind. I thought there was something kind of irreverent in [Diana’s] answers. I could see her meshing with Tyler.
So we roped in Diana, whose application described her as a “renaissance girl” looking for a guy with “a side of smart [aleck],” and sent them off to Sette Osteria in Dupont Circle.
Diana: They sat me down, and a minute later [Tyler] got there. He was very smiley and happy. He has pretty crazy hair — I mean that in the nicest way possible. He’s a little bit different from my usual type. I usually date super bro-y guys, for lack of a better word — tall, athletic people. He’s getting a master’s in fine arts, so he’s more the creative type.
Tyler: At a superficial level, I was like, All right, Mom! Thank you! [Diana] would absolutely have caught my eye in any context, no question about it. She seemed from the get-go — and I find this incredibly sexy and fantastic — just really comfortable and confident in her own skin.
Diana: He told me his mom had picked me out of a group. I was very complimented. [But] it’s funny, because I actually didn’t write my application — somebody else wrote it. My best friend from high school was really excited when I moved back here and basically made me do it. Maybe she just made me seem more wonderful because she wrote it and I didn’t have to be modest for myself.
Molly: I tried to make it sound like Diana — she’s smart and funny and great. I was so excited when I heard she got picked. Do I get some credit?
Tyler: We didn’t have to work too hard to find commonalities. Someone who is quick and willing to laugh is important to me, [and] things were pretty light and hilarious throughout.
Diana: The conversation was easy, and we got along really well. We talked about different types of creativity. I write and he writes, but we do very different things: I write proposals for work, and he writes poetry. I was saying I didn’t feel like what I did was [creative].
Tyler: She said she didn’t think of herself as a particularly creative person. But judging from our conversation, I immediately knew that wasn’t true.
Diana: We left dinner at 10:30. He was saying [Black Cat] had a burlesque show. I thought, That sounds fine. I’m up for anything. And I appreciated that he thought of something more creative than going somewhere for another drink.
Tyler: I’d looked into a few different things that might be interesting to do. I’d never been to one. I brought up the idea, and she seemed instantly receptive and curious and agreed this could be a funny way to spend the evening.
Diana: We called his mom [on the way there].
Tyler: It was Diana’s idea. Which showed real moxie.
Fay: The first thing I said was, “I don’t think this bodes well if you’re calling at 10:30 at night.” He said, “Hold on, someone wants to talk to you.” [Diana] thanked me for choosing her [and] said they had a wonderful time. I felt good about that.
Diana: [The burlesque show] was definitely a new experience for me. It was a little risqué. But I’ll do anything once. We got called up onstage.
Tyler: We were given feather boas and taught a simple, if sexual, dance. It was a decidedly goofy experience.
Diana: We left when the show ended. I’m not going to kiss and tell! I’ll leave it up to him.
Tyler: It was a goodbye-hug scenario where our faces were just very close, and I sort of said, “I think I’m going to kiss you now” and kissed her. It wasn’t necessarily my smoothest moment, but I’d like to think it was at least marginally endearing.
Diana: I would give it a 4. I feel like a 5 is such a high compliment! We were saying people [in Date Lab] always rate the date so high. It’s Date Lab grade inflation.
Tyler: I can’t imagine feeling more comfortable or at ease, and for that matter attracted, both physically and mentally. I think it’d be disingenuous to say anything less than 4.5.
Tyler and Diana got together for lunch at Union Market followed by a backyard barbecue at his place (in honor of his roommate’s birthday). They also hung out when they ran into each other at a bar. But though Tyler reached out to suggest another date, Diana’s ready to move on: “He’s a great guy, but I think I’m just interested in being friends,” she says.
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