She came face-to-face with Drew Gilbertson, the 24-year-old software developer we set her up with, at Alta Strada, an Italian restaurant on K Street NW. The first impressions were positive. Drew said he thought Katherine was “very pretty”; Katherine thought Drew was “very cute.” Drew was impressed that Katherine took charge of the conversation early on, while he was still feeling nervous. “I’m used to going on these things and having to carry the conversation,” he said. He doesn’t generally mind doing it, but in this case, “not having to do that was really cool and really nice.”
Early on in the date, Katherine said something — neither of them can remember what it was, just that it was very deadpan, and very much his sense of humor — that caught him off guard, and when he realized she was kidding, he visibly relaxed.
Faced with a man who, in person, did not seem like a serial killer, Katherine came clean about her attempted background check on him. Laughing at her hubris, she told him: “I tried to find you on LinkedIn.” Drew, she recalled, told her: “If I was trying to murder you, I wouldn’t put it on my LinkedIn!” To which she said: “I don’t know, maybe you’re a serial killer who wants to network with other serial killers!”
“It snowballed into this not very funny, funny joke,” Katherine said.
The talk of serial killers didn’t slow things down. They were so busy talking that they kept forgetting to look at the menu. Their poor server came by four times. It took them almost 40 minutes to order. When they were finally ready, Drew was happy to hear Katherine admit that she hated wine. He’s not a wine drinker either — so they ordered beer instead. Both were weighing the potential deliciousness-to-disastrousness quotient of pasta on a first date — “I had an intense internal debate over whether to eat pasta. You don’t want to look like a fool eating spaghetti,” Drew told me later. But by the time they were ready to order, both were willing to risk it.
She got the spaghetti; he got the tagliatelle. They talked about their shared love of sci fi and their favorite TV shows. Katherine, a recreational boxer, impressed Drew with her passion for her work and hobbies, and he appreciated that she kept things light and fun. Katherine found it sweet that Drew, who plays volleyball and kickball and recently took up sailing, kept getting interrupted by texts from his sisters, grilling him for details on the date.
They also talked about their mutual distaste for the D.C. dating scene. Katherine really values vulnerability, and she often feels it’s lacking in a city where so many people are trying to promote themselves. Going into the date, she said, “I was trying to decide how vulnerable I should be with this person, and whether it would impact the date. It’s something I want to be doing more of. My mind was spinning a bit. How much do I share, and how much will he share with The Washington Post?” Joking around had helped her feel more comfortable about opening up, and it seemed to warm him up, too.
A couple of hours into the date, they looked up and realized that no one else was in the restaurant. It was about to close, so they split a quick dessert, but they weren’t ready to end the night just yet. They took a walk and kept talking. They discussed how awkward it was to end a date. Thankfully, this ending wasn’t that awkward: They both said they wanted to see each other again.
“What I think is the key to a good date is, do you have inside jokes by end of the date?” Katherine said. “We did, which was really funny. I’ve never had that happen before.”
The morning after the date, they were still texting — and still making jokes about serial killers.
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After a second date, Drew and Katherine decided they weren’t a match.
Marin Cogan is a writer, senior producer and co-host for Pop Up Magazine.