The Maxim Guide to Hitting On Girls

Need help hitting on girls? A professional wingwoman reveals her secrets.

Need help hitting on girls? A professional wingwoman reveals her secrets.

Meet The Clients

Jack is fidgeting, telling a woman that he wants to get married, now, while Eric is striding toward a group announcing, “I want a superhot girl.” I’m trying to figure out which one to rein in first, but, hey, at least neither of them has thrown up on me yet.

When I applied to be a wingwoman for New York Dating Coach three years ago, all I knew about the business was what I’d seen in Hitch. I imagined I’d be a white, female Will Smith, helping the sweet, awkward Kevin Jameses of the world. It seemed simple: Forty dollars an hour for three-hour sessions in which I’d accompany one or two men to bars and help them strike up conversations with women.

Plus, before I get to them, New York Dating Coach has already spent hours preparing my clients for their foray into the dating world. It’s less a matchmaking or dating service than a tutoring program in the art of successfully meeting and connecting with people you want to bone—er, date. So by the time I meet up with Jack and Eric, they’ve rehearsed conversation topics, improved their wardrobes, and learned to tailor their behavior to different settings. (Picking up a woman in a bar is different from picking up a woman in a library.) They’ve had practice sessions in coffee shops, and now the graduates are ready for a night with me.

At this point my job should be easy, right? But basic training doesn’t always make you combat-ready. I’ve had a superhot client so consumed with social anxiety he really did puke on my shoes. And I’ve been out with a totally average-looking guy who hit it off with a semifamous musician. I left him in the wee hours surrounded by models.

With Jack and Eric, I had no idea what to expect. But I knew I’d need every weapon at the ready. Now I’m going to let you tag along on our night and learn my tricks for free.

The Debriefing

I meet the guys at a restaurant in a trendy neighborhood. Both are well-dressed in button-down shirts, clean jeans, and leather shoes. Eric, cute if a little short, is a tech entrepreneur in his 20s who just sold his company to Facebook. “Growing up I always worked hard at school,” he says. “I figured that when I was successful I’d get really hot girls. Now I’m successful, but I have no idea how to talk to hot women. I just want to date a 10.” Eric’s goal may seem like a challenge, but he doesn’t realize that it’s easy to meet extremely attractive women, because they expect to be approached. You just have to make them feel like you don’t want to talk to them only because they’re hot.

Jack is trickier. He’s in his mid-30s, his friends are married, and he has no one to go out with anymore. His shirt is buttoned to the chin, he’s nicked himself shaving, and he keeps staring at his shoes. Ready to settle down but shy, guys like Jack make great boyfriends once they find a girl. I hope to come upon one woman he really hits it off with.

Since they’re well-dressed, we can head to a quieter, upscale bar—more dry martini, less PBR—which attracts more receptive girls: They haven’t just wandered out to get a beer; they’ve dressed up for a night out and are hoping to be approached. We hit a lounge with no sign outside. (It’s easier to meet people in places that feel exclusive, because everyone there already believes they’re in a semi-secret club.) As we spot a circle of five attractive girls—a definite 10 who looks like Jessica Alba as well as some girl-next-door types who might be a better match for Jack—I ask the guys how they’d approach.

“Maybe,” says Eric, pointing at the 10, “I should neg her?” Ugh. No. If a woman is going to leap into bed with someone who just insulted her to prove that she’s attractive, she’s probably lacking self-confidence. And possibly sanity.

“But isn’t it good to throw girls off guard?” Eric asks. Sure. You can’t just go up to a woman and say, “Gosh, I think you’re so pretty. Won’t you be my girlfriend?” No one wants a puppy dog. In a way it’s rude, because it seems like you don’t care if she’s Mother Teresa or a serial killer as long as she’s hot. And it’ll make her think she can push you around. Besides, smart, desirable women don’t go for men who try to make them feel insecure. All that does is reveal how anxious you are.

I decide to strike up a conversation. “Don’t focus on the superhot girl,” I say. “Go for one of her friends. They’ll like you more because they’re sick of men only hitting on her. And she’ll wonder why you’re not hitting on her.”

Best Intros for Single Gals and Groups

When it’s just one girl, I simply go over and say, “I’m sorry, but my friend thinks you’re really cute.” This has never not worked, and I think every man should enlist his female friends to do it on his behalf.

Approaching a group is harder. I take a swig of my drink and loudly exclaim, “I can’t believe we’re even arguing about this! Anyone can see there’s a right answer!” Now I pose a question to the girls to: (1) show that the guys have ideas, and (2) make the girls feel the guys care about their opinions and not just their looks. I turn to the Amazonian blonde and say, “Italy or Japan: Which would you rather visit?”

She pauses. “Japan.”

“See?” I say, turning back to Jack and Eric. “The obvious choice.” (When posing random questions to a woman, always agree with her. Psychologically, it sets you two up as a team.) “My friend is planning his next trip, and he’s torn between the two,” I explain. The blonde starts talking about how she went to Japan, and, poof, we’ve broken into their circle. Eric glances at the blonde, a 10 by any standard, but gravitates instead toward her slightly less attractive friend, who looks thrilled.

Jack turns to the blonde: “Venice would be nice for a honeymoon.”

She’s already freaked out. “Ha!” I exclaim. “Jack is great. Did he tell you about the last time he went to Italy? It’s a funny story.”

I’m desperately hoping Jack has a funny story. Ideally the kind about how he was out at a cool place (he goes to cool places!) with his friends (he has friends!) and there was a minor but comical misunderstanding. A tale about the time you got wasted in Bangkok, got in trouble

with prostitutes, and a person ended up dead is hilarious, but you can’t tell that story the first time you meet a girl. She won’t hear “funny,” just “Bangkok, prostitutes, death.”

The Results

The challenge with good guys like Jack is transforming them—not into a “bad boy,” but into someone who isn’t quite so eager. “When you’re talking to women,” I explain, “don’t think more than a week in advance. Just see if you like the same restaurants, not if you want the same number of children.”

Since Eric’s doing well with the group—he’s got them laughing—I steer Jack to another cluster and ask them for bar recommendations (another opinion question). He’s nervously folding his cocktail napkin into smaller pieces. I smile and sustain the chat until he starts talking about places he likes around town. Victory!

By night’s end Eric has seven numbers—way beyond what I expected—and is standing taller. And Jack has found two girls who seem really into him. I’ll probably never see these guys again, but I feel good knowing I helped both of them a little bit. Like Hitch. Sort of.