Drunk Woman Mistakes Authentic Preppy for Ironic Preppy
Nate Orosco’s “Dirty Thirty” birthday party was, by all accounts, a success. Not least of all for Monica Dehner, who met a cute boy somewhere in the vicinity of her fourth glass of limoncello. “It was a party, so it’s not like we went that deep,” says the 29-year-old graphic designer of Clay Walker, a 27-year-old law school student. “But I think we talked about Casper, my French bulldog, and how much we both think the butterfly stroke sucks.” Mostly, she admits, she was attracted to his style: he was tall and tan and wore seersucker shorts, a blue oxford shirt, and a pair of Sperry Top-Sider boat shoes. “I guess I was probably reading too much into his clothes, but I just assumed that he would be into certain things. Like, maybe he would like Whit Stillman and the Dirty Projectors, or, at the very least, Wes Anderson and Vampire Weekend.”
The following Monday, Mr. Walker called Ms. Dehner to ask her out on a date. “That’s what he called it, ‘a date,’” she says, shaking her head and sipping a lemon verbena iced tea. “I should have listened to my gut instincts then and there and realized that was a red flag. Who, like, gets my number, calls me, and asks me on a date? Is this Mad Men? But I guess I was kinda flattered, so I said yes.” They met, per Mr. Walker’s suggestion, at Corner Bistro. (“I knew the burgers there weren’t organic or anything, but I didn’t want to be that person on a first date, so I didn’t say anything,” Ms. Dehner notes.)
The problems began immediately. While locking up her Jorg & Olif bike, Ms. Dehner saw her date approaching from a distance. “At first I thought Clay was wearing khakis. I thought there was no way that would be possible, but as he got closer and closer, I realized he was definitely wearing khakis. Khakis with pleats! And one of those Polo shirts with the giant logo the size of your hand,” she says, shaking her head. “I told myself that maybe he was making some kind of weird, meta statement about how much first dates resemble job interviews, so I just kissed his cheek and we went inside.”
Once seated, the talk turned to what they had done the night before. “I told him I had gone to this Todd P show at Death By Audio and he asked me who Todd P was and then—oh my God, this is so bananas—he told me he had gone to some Murray Hill bar with his old teammates from the Middlebury lacrosse team! That’s when I knew this was never going to work.”
Ms. Dehner struggles to identify the kind of men she normally becomes romantically involved with but points out that she met her college boyfriend at the Situationist food coop they both belonged to at Antioch College, that her next boyfriend was a DJ who primarily played Italo Disco, and that the last boy she went out with wooed her via VHS recordings of Dave Kendall-era episodes of MTV’s 120 Minutes. “Look, I don’t want to call them hipsters, she says, trailing off. “But they are all kind of hipsters. I just thought Clay was one too, since that’s how they’re all dressing this summer.”
To be sure, men and women who live in urban environments and consider themselves creative have appropriated a variety of fashionable totems over the years, from Vans checkered slip-ons and trucker hats in 2003, to keffiyehs in 2006, and more recently, Ray-Ban Wayfarer sunglasses and moccasins in 2008. The danger in the recent upsurge in classic preppy styles is that, while Ms. Dehner has relatively little contact with professional dancers who might have worn the Repetto jazz shoes that were so popular in 2007, she apparently has authentic preppies—Mr. Walker emailed this reporter only to confirm that he is, in fact, a graduate of Choate Rosemary Hall—in her social midst.
The rest of the date went by in a blur of awkward conversation about the latest Batman movie. Three days later, Mr. Walker called Ms. Dehner to ask her to dinner at a restaurant on Park Avenue South, but she declined, explaining that she had recently gotten back together with an ex.
