My name is Meg, and I’m your perennially single friend. You know, the one who helped you move, threw an epic bachelorette party for you, and went to a company cookout with your cousin Brad after his date dumped him (you still owe me big for that). But I’m thirty-one now, and my dating history (Brad included) has been a bit pathetic. So I turned to two local dating experts: Jula Jane, a blonde, finely kempt executive matchmaker (i.e., she connects people in Ted Turner’s tax bracket) and author of Secrets to Date By, and Sarah Kathryn Smith, the chatty brunette founder of the Eight at Eight Dinner Club and One on One Matchmaking.
I joined Jane and Smith for lunch and soon discovered that meeting a dating expert is like having your bikini line waxed: It’s painful, embarrassing, and too intimate for strangers. They immediately tried to mine out why I’m still single, grilling me about my life, likes and dislikes, and dating history. Finally, Smith pointed at my cleavage and said, “Well, you’re already doing something right.” It unnerved me a bit that both Smith’s and Jane’s relationship advice could be pulled, word-for-word, out of dialogue from Mad Men. “Men work harder to have more money, more power . . . to have a wife, a better life, a better family,” said Jane, a divorcee now newly engaged. “Same with a woman—we want to be beautiful and the best we can be to attract the best person.” It’s a little depressing to equate love with a primal need for your genes to live on, but I paid attention to Jane’s rules: You must not initiate conversation. Instead, get men’s attention by means of a “sexy look” and attitude. (This is worrisome; “sexy” on me could be misinterpreted as “bad heartburn.”) Keep the conversation focused on him. Remain “mysterious.”
The still-single Smith agreed: “You have to play games. You can’t be yourself right at the beginning. You have to present yourself in a way that would be attractive to the other person.” Her other edicts: Don’t talk about your exes. (Easy, there aren’t many!) Don’t accept a date at the last second; look your best; let them pay. Smith disagreed with Jane on one point, though: It’s okay to approach a guy, as long as it’s with a compliment. “Say, ‘That’s a lovely watch,’ because I can guarantee they sweated over that $3,000 purchase,” suggested Smith. Jane then offered to set me up with one of her clients, and Smith offered one of hers as well.
While waiting for my dates to call (because a woman, upon pain of death, is not to call a man first), I decided to practice my “sexy look.” My first attempt garnered me a bowl of butter at the IHOP. I had only asked for an extra few pats, but hey! As I imagined what other food items my smoldering eyes could procure, Jane’s client texted me—and I panicked. If he texted me first, does that mean I can call him? Should he text twice before I call? What is the appropriate text-to-phone-call ratio? What would Jula Jane do? Constrained by rules, I was too flustered to respond. The date never happened.
I had high hopes, though, for my date with Smith’s client, a computer programmer who needed someone who would embrace his “inner nerd.” That sounded right up my Battlestar Galactica–loving alley. I followed Smith’s advice and spent thirty minutes Googling men’s watches, but it turned out I should have researched obscure comic book illustrators instead: After an hour with Doug, I realized we weren’t even in the same nerd galaxy. If he were Darth Vader, I would be the Star Wars stormtrooper whose only line is, “Look, sir: droids.”
I decided it was time to try out the experts’ tips on my own. Smith had suggested meeting men at Turner Field—specifically, the Chop House’s busy bar—so that’s where I headed. And there were plenty of men there. But no matter how much I coquettishly smiled or fidgeted with the straps of my soft-pink sundress, they were more into the game. I did come away with this: Baseball trumps cleavage, and never wear Spanx to a sporting event. Ever.
Though my post-expert dating attempts were all strikeouts, I wasn’t that upset. All this “mention his watch” and “never call first” advice was worth a shot, but it didn’t feel organic. After all, it’s just like my mom says: “It’s better to be rejected for who you are than accepted for who you aren’t.” Maybe I will keep practicing my “sexy look,” though—you never know when you’ll need a bit more butter.
>> DIARY: Read about how Meg Donahue fares as she experiments with more flirting techniques from Jane’s Secrets to Date By
Photograph by Alex Martinez