Dating Diaries Challenge: The Art of Flirting

By: Kelly DiNardo

This past Valentine’s Day, Jason Tesauro, coauthor of The Modern Gentleman and The Modern Lover, hosted “The Art of Flirting” at Ici Urban Bistro. The event promised “to set off sparks amongst singles and bring back the butterflies in couples.” We sent Max Schwartz and Michael Amesquita to test it out. Here’s what they discovered.

Max and Michael met at a bar before heading to the event. They were attending together for moral support, not as dates. Unfortunately, the organizers missed that small detail. After an introductory cocktail hour in which Max and Michael realized they were two of only five single people at the event, they were seated together for dinner. Just the two of them.

“Under each person’s plate, there was a construction-paper heart with a challenge on it,” says Max. “Both of ours were totally inappropriate for two single people. The challenges were to hold our date’s hand and stare into each other’s eyes for ten seconds. Michael and I were totally disrupting the room because we were laughing so hard.”

During dinner, Tesauro gave a three-part lesson on the art of flirting. In the first part, he introduced the event, read a passage from his book, and opened a bottle of wine by sabering the top off. In the second, he talked about the do’s and don’ts of dating. The third part was about what Valentine’s Day is and why it matters.

Max was unimpressed: “The guy who was supposed to be our guru to flirting was a total creepster. He wasn’t a jerk or anything; he just kept trying to insert seductive words into his shtick.”

More important, the advice “just wasn’t anything I hadn’t heard already,” Max says. “The advice was beyond obvious. It was ‘Compliment girls on their outfits, don’t be too handsy.’ I don’t think I learned anything particularly impressive about the art of flirting. If it’s all about the modern gentleman, I would have liked for him to talk about things like texting and e-mail.”

Max did walk away with a parting gift: “He gave me a copy of one of his books, which is a gold mine of hilarity. He has two books—The Modern Gentleman and The Modern Lover. They’re written in the most unbelievable purple prose and suggest things I would never do as a human being. There was a section on how you should order for your date. Maybe this is why I’m not a successful dater because I’m not doing these things that seem ridiculous. Maybe it’s a generational thing. It just seemed so archaic.”

Michael thought the way Tesauro described things was cheesy, but he liked the throwback feel to it: “I think bringing stuff back from the past is good. He mentioned getting up when a girl arrives or leaves the table. He said you can just do a small stand. I might start doing that. I think it shows respect for women. In general, I think we should acknowledge and treat people better.”

The big problem for both of our daters was that despite how the event was billed, it was really geared toward couples. There were three other singles—two girls and their male friend. But while the guy kept claiming he was just a friend, he ended up rather protective of the cute brunette in the group. Michael did connect with the blonde and got her number. He’s planning to call her this week.

“It wasn’t a miserable experience,” says Max. “The food was really good. And if nothing else, it’s an amusing story.”