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How To Pick Someone Up

Need something new in your arsenal of ice-breakers? Try these expert-approved moves—and see how they helped some savvy singles succeed.

By Matt Christensen

“Come here often?” “Can I buy you a drink?” “Mind if I join you?” Yup, most of us have used these lines at some point, if not many points, in our dating lives in an attempt to captivate the attention of some cute stranger. And while these ice-breaking basics can certainly get the job done on occasion, some single people out there might be wondering: Is there anything more sophisticated I can try? According to Neil Strauss, author of The Game: Penetrating the Secret Society of Pickup Artists, there are plenty of ways to hone your pickup skills and increase your chances of swapping phone numbers. Here, see how some single folk flirted successfully—and learn how you too can pull off their moves.

Singles' Best Pickup Tricks
More original approaches that reaped great results.

Hats off to you
“I never leave the house without my cowboy hat. Once I was at a bar, and I saw a girl I was interested in, so I went over to her and, after introducing myself, I let her wear the hat. I told her she’d better not run away with it. Her response? ‘You don’t have to worry about me leaving.’”—Deaq Mattison

Good studies
“A friend and I went up to random guys at a bar and told them we were doing a survey. We asked them all kinds of questions like, ‘Do you prefer to be approached or do the approaching?’ and so forth. By the end of the night, most of the guys probably knew it wasn’t a real survey, but no one minded—and we got a few numbers.”—Kate Balser

Passing notes
“I was at a club with my married friends and no one would flirt with me. So, I wrote ‘Single and Shy: You Make The First Move’ on some cocktail napkins and handed them out. One guy came over, and we talked all night and swapped numbers.”
—Dana Miller
Be quick
A case study: “I started off a conversation with a girl at a bar by saying, ‘My friend drank too much and feels sick, so I have to drive him home in a few minutes, but I wanted to introduce myself before I left.’ She said she admired me for taking care of my friend, and after flirting for awhile, she asked me if I was planning on coming back after I took care of him—which I did, of course!”
—Rick Sanchez

The pick-up lesson learned: If you try to start a conversation with any hesitation, stammering, or other time-wasters, you may well be shot down. Speed is your friend—as is being direct. “Give yourself a time limit,” says Strauss. “Say, ‘I only have a minute, I have to rejoin my friends soon, but I wanted to come say hello.’ People will be more apt to listen to what you have to say, because they don’t feel intruded upon”—and they won’t be as concerned that you are going to be lingering next to them all night. Hopefully you can display enough personality to make them want you to stick around—if so, just say, “Looks like my friend got his second wind and wants to stay” and you’re golden.

Keep some fun facts on hand
A case study: “I was eating lunch in the park next to a really hot woman one day. I had a bottle of Snapple, and on the underside of the cap it said that a goldfish’s attention span is roughly three seconds. I leaned toward her and pulled a ‘did you know?’ She was surprised at my straightforwardness but laughed. While we didn’t speak about goldfish anymore after that, we did talk for another hour, and I got her number.”
—Jon Thompson

The pick-up lesson learned: All those lonely nights you spent watching Jeopardy may finally pay off. According to Strauss, “All useless information is useful. Fun facts like ‘Hey, did you know that the average woman uses eight pounds of lipstick in her lifetime?’ can be a great conversation-starters,” provided, of course, that you offer it up with a casual smile and a gleam of interest in your eye. Not only will you win points for originality, these factoids serve as excellent distractions from the fact that you’re, well, hitting on them.

Impress their friends
A case history: “I was at a sports bar with some friends when I noticed a group of people at another table watching the same football game we were. There was this really cute girl, some of her girlfriends, and two guys. On my way to the bathroom, there was a great play in the game, and everyone started cheering. I stopped right next to the girl’s table and talked sports with her guy friends. From there, I got introduced to her girlfriends, and then to her. Turns out she was a big sports fan too, and we ended up talking for the rest of the game. Her and her crew showed up at the bar the next weekend, but this time she came to sit with me.”
—Bret Irvin

The pick-up lesson learned: You’ve got your eye on some cutie who’s enjoying a laugh with some pals. What should you do? “Don’t hit on the person you want,” warns Strauss. “Instead, befriend their friends.” Since you’re not interested in dating these people, you’ll be at your most comfortable and confident. Plus, the object of your affections is bound to let down their guard after seeing you bond with the posse. Sooner or later, someone in the group is bound to introduce you two, and if not, just say, “I feel like I’ve been snubbing your friend; mind if I switch seats and talk with her for awhile?”

Forsake the flattery
A case history: “I saw a really gorgeous girl at the grocery store. What caught my eye wasn’t how pretty she was, though—it was the piece of toilet paper stuck to her shoe. I walked over and said ‘I like your shoes, did they come with the toilet paper?’ She was so embarrassed, but we were both able to laugh it off. I think she liked the fact that I wasn’t straight-up hitting on her and, in the end, we exchanged numbers. I went out with her a week later.”
—Tyler Stone

The pick-up lesson learned: Good-looking people get swooned over all the time, which is why you should avoid doing it at all costs. A better tactic? Try gently picking on them instead, as if you were their older brother or sister. Tell a woman that she has lipstick on her teeth, or point out to a guy that he’s the only man at the bar drinking wine, not beer. They’ll be thrown by your gentle dig and be eager to change your opinion. “It takes a lot of confidence to use what’s called a neg, but it’s a great trick,” says Strauss.


Matt Christensen writes for Maxim and other publications. He’s used the “hat trick” with great results himself to pique a woman’s interest.
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