As a dating coach, I know first dates are always awkward, but when you add being aware that your words will appear in The Washington Post, it can take a little longer to shake that uncomfortable feeling. In the case of Ben Dobkin, a 26-year-old analyst at a tech company, and Claire Goldberg, who is 24 and works for a progressive nonprofit, it took about half of the 90-minute date to settle in to a natural flow.
Without even realizing it, Ben leaned into some of the tips I give my clients for virtual dates. First, he cleverly found out in advance the kind of food that Claire would be ordering so he could order something similar. A detail that he found a little embarrassing but I read as thoughtful and charming. I advise clients that ordering the same meal is an excellent way to create a shared connection on a distanced date. Fortunately, they are both fans of Italian food, and coincidentally (or not) both ordered burrata ravioli.
The next thing I advise is to let your curiosity drive the conversation while being a good listener. Ben demonstrated this by noticing an interesting museum print behind Claire. She shared that it was from a trip to Paris, which dovetailed into a conversation about Ben’s adventures in Tanzania, in addition to his love for the Berkshires and his desire to settle one day in western Massachusetts.
One of the most important qualities my clients look for is a shared sense of humor, and that is where the conversation turned next. Ben’s and Claire’s TV-watching habits vary greatly, but they did engage in a conversation about “Saturday Night Live.” They agreed that SNL is no longer funny but debated about the exact moment when it last was actually funny. According to Ben, they landed somewhere between when they were both in high school or college and never.
All the while, Claire’s Chihuahua, Pistachio, whom she had rescued just a couple of days earlier, sat peacefully in her lap. A lifelong dog lover, Claire had to know if Ben was a dog person or a cat person. “Neither,” Ben replied. He went on to explain that he liked animals but he never grew up with them so he didn’t have a particular preference. He did reveal, however, that he just adopted a pet rock. His name is Doug, and he has his own Instagram account. Claire seemed to gloss over this detail, and when I asked her why, she responded, “I thought it was weird.”
Intelligence is another quality that most of my clients put on their must-have list, and Claire was impressed by Ben’s Ivy League education. Leave it to a Princeton man to ask his date what she’s reading. Claire mentioned that she was reading a collection of short stories by Kurt Vonnegut. This was music to Ben’s ears, as Vonnegut is his favorite author. Somehow this translated to Ben as “We both shared the same favorite author,” but Claire wouldn’t quite take it that far.
For years I’ve told my clients to avoid talking about politics on the first date, but in D.C., and in a year like this one, that’s somewhat impossible. Plus, for Claire, who worked on the campaigns of Kamala Harris and Hillary Clinton and is passionate about progressive issues, where someone lands on the political spectrum is very important. So, she flat-out asked him, “Who did you vote for in the Democratic primary?” Ben stammered a bit. He revealed he admired Andrew Yang’s ideas but didn’t end up voting in the 2020 primary. As Liz Lemon would say, “That’s a dealbreaker” for Claire.
By this time, the conversation had started to drag and Pistachio needed to go outside to do her business. Ben asked for Claire’s number and texted her while they were still on the date to make sure she received it. A few minutes later, they said good night and signed off. Ben wasn’t sure he felt sparks, but because of the awkwardness of a first date, he was willing to give it a second chance.
Claire had a burning question that couldn’t wait: “I had to know what he thought of Andrew Yang running for New York City mayor.” She texted Ben that one question after the date.
Not surprisingly, as part of the Yang Gang during the presidential race, Ben declared his admiration for Yang and confidence that he could be the right person to run the city. Then he followed up with, “Totally fair question but only if you share your thoughts as well.” Feeling that there are many other candidates (in particular women of color) who would make better mayors, Claire was put off again by Ben’s politics and couldn’t bring herself to reply.
“Even though we disagreed on things, it was a fine date,” Claire later admitted to me. Yet this last text exchange confirmed that she couldn’t give a second date a vote of confidence.
Rate the date
Ben: 4.25 [out of 5].
No further contact.
Damona Hoffman is a certified dating coach and host of the “Dates & Mates” podcast.