Charmed, I'm sure

The last five years have seen a glut of dating trends come and go. Some, like online dating, have become a classic way to hook up. Others, like Dinner in the Dark—a recent London export in which anonymous singles dine with the lights off, served by waiters in night-vision goggles—are probably too absurd to ever catch on. I decided to test out the newest trend: flirting classes.

The intent is not to hook you up with someone specific, but rather, to teach you playful come-ons to improve your own romantic overtures. There are a few programs out there, including “Flirting for Nerds,” a workshop offered by Andersonville’s woman-owned sex shop Early to Bed (www.early2bed.com), and “Flirting and Walking” (www.allureseminars.com), a weekly walkabout led by dating expert Jean Smith, who hits spots in Old Town as she doles out advice on flirting techniques.

But for more personalized instruction, I turned to Patti Feinstein (www.pattifeinstein.com), the flirting workshop instructor who’s dubbed herself “America’s Dating Coach.” Feinstein got into the professional matchmaking business in the early ’90s but realized it wasn’t just a hand-delivered hookup clients needed. “I was appalled,” she says. “People needed more than an introduction—they needed to learn how to date, and how to adjust their attitudes.” For $100 an hour, Feinstein says she can transform awkward singles into smooth operators. One method is “wing service,” in which she joins you out on the town, coaches you on what to say and do, and in some cases even approaches the guy or gal you’re scoping out to gauge interest.

After answering the phone in a silky but stern alto voice that scares me into submission, Feinstein issues a list of commands to follow before we meet—most notably, choice of apparel: a low-cut blouse accessorized with a few long necklaces. “Oh, okay, why?” I sheepishly ask, mentally scanning my closet, in vain. “Because we’re going to practice by picking up men in Best Buy.” Suddenly, visions of the video-game aisle appear: I’m trying to land a date with lines like “Oh, you love Super Monkey Ball Adventure, too?”

When we meet at Starbucks the next day, I’m more than mildly anxious to start picking up men in a new low-cut shirt—modestly covered with a cardigan. “Relax, open yourself up,” Feinstein instructs. Inviting a few startled glances from coffee drinkers, she demonstrates how to dangle a necklace to draw attention to the chest, and to point palms away from the body to show off forearms—apparently, an unlikely erogenous zone. I try to imitate her but instead resemble a drowning bird, limbs flailing. “I don’t think we should practice picking up men today,” Feinstein says. Instead, I work on mannerisms in big crowds. Feinstein says to pretend it’s your party and you’re the hostess: Be nice to everyone, give your name, chat for a moment (no politics or Iraq war) and leave. “Don’t ever scrunch up your face and say ew,” she says. “If you don’t like someone who asks you out, tell them it’s a compliment and move on.”

The next night I put Feinstein’s advice to the test at Flirt with Flavor (www.chicago.flirtwithflavor.com), a monthly Lavalife singles event at Reserve nightclub. I down the free Absolut drinks at the bar while channeling a 1950s hostess, then totter off to greet my “guests.” The first stammers something about these things being weird, which seems boring and obvious. I give my name and proffer Feinstein’s words for an amicable exit: “I’m going to sit down at the other end of the room. But it’s really great to meet you”—oozing with kindness, as instructed.

Surprisingly, it works. He smugly grins, satisfied with the compliment. Continuing onward, I approach half a dozen more men. Then I get to Chris, a tall guy in jeans clutching a clipboard. “Why are you here?” he asks. “Oh, you know, just checking things out. And you?” I inquire, keeping my cool and feeling foolish while groping my long necklaces. “I’m a reporter,” he says. “I’m writing a story on this, and I don’t need to go to these things to get a date.” Ouch. But rejection happens to every host, Feinstein had cautioned, advising me to be gracious about it. Head held high, I mingle a little longer before leaving, exhausted, ego slightly tarnished, but with a skill that will likely—as evidenced by the numbers in my pocket—come in handy one day.