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The Art Of The Pickup


If you’re returning to the dating scene after some time off and are ready to hone your skills, read this advice from in the trenches.

By Margot Carmichael Lester

f you’re dipping a toe back into the dating scene after a long break (be it a relationship or a marriage that’s now in the past), we know those questions circling through your head. “Who? Me, flirt?” and “Do I have to act like someone off of a reality show?” Relax: You can get back in the swing of things without dancing on tabletops or tossing off an array of often-practiced lines.

“What is really required is an attitude adjustment,” says Shoshanna Rikon, a professional matchmaker. “Get out of your home, and start enlarging your social circle.” Rikon suggests getting started by making a list of your interests and setting social goals. “Single men and women need to treat their social lives
“Don’t act too cocky or arrogant. That’s the best way to turn a woman off.”
with the same type of excitement and passion that they put toward their jobs,” she urges. “Once you have a social to-do list or a plan of action it is much easier to be proactive.”

Another tip: Assemble a group of friends who share similar interests. “That way,” Rikon explains, “you will always have a wing-man or wing-woman to help accompany you to fun events where you will invariably run into other singles.”

Now it’s time to get busy making contact.

Don’t fear the turn-down. Nobody likes getting shut down, but you have to get over your fear and go for the ask. “The key to success in social situations is to be confident in who you are and what you are about,” Rikon notes. So give yourself constant affirmation. “Remind yourself of why you are special and loved by others.” That said, men take note: “Don’t act too cocky or arrogant,” says Delilah McGinnis of Denver. “That’s the best way to turn a woman off.”

Smile. Ask your friends to check out your facial expressions next time you’re on the prowl. You might be surprised to learn you’re not smiling. “People only approach people who’re smiling,” says Jill Spiegel, flirting expert, author and host of The Jill Spiegel Show. “It’s a great way to start a connection." Practice your smile at home so it looks natural. “Nothing’s worse than a Cheshire Cat grin or a slightly sketchy smile,” says Tom Barnes of Phoenix. “It makes you wonder if there’s something wrong with them.”

Get out there. Instead of watching the game at home or with your buddies, go to a local sports bar. Attend gallery openings. Go to readings. Join a health club. “You can start a conversation so easily with things you have in common,” Spiegel notes. “So turn to the person
Check your smile at home to make sure it looks natural, not sketchy.
next to you and ask a question.” Here’s an example: “Did you see that play, that was incredible!” or “How many of his books have you read?” or “Would you spot me on the bench press?” (One note if you’re doing your mingling at a sports bar: “If I’m really into the game, I don’t want to chit-chat, even with a hot girl,” admits Mike Juliano of Chicago. “Wait till a commercial break or join me in cheering after a great play.”)

Tell the truth. Cute come-ons not your thing? Don’t worry. “The most effective line is an honest introduction, like ‘Hi, my name is David. What’s yours?’” says Zannah Hackett, author of The Ancient Wisdom of Matchmaking. Then find something that genuinely stands out about the other person. “People appreciate real conversation about real obvious details.” Need a specific example? “A guy once told me I had lovely hands,” recalls Suzette Baker of Nashville. “It was such a unique compliment that he definitely got my attention—and my phone number.” And just remember, “A clever cliché or dishonest remark leaves people feeling like they’ve just been slimed,” says Baker. “Not a good thing for making a positive impression.”

So summon up your courage, put on your game face and get out there! You might just find that your next outing nets the ultimate prize: true love.


A guy once tried to pick up Carrboro, NC-based writer Margot Carmichael Lester by holding up a black lace undergarment and asking, “Is this yours?” His overture was rebuffed.
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