How To Succeed At Picking Up Women (And Fail At Keeping Them Around)

By Playboy.com Staff

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Pulled from our best (and worst) dating experiences, we created a game plan for all the V-day singles hoping to get lucky.


It’s not every man’s pleasure to have a Bunny of his own to nuzzle up to on Valentine’s Day.

Whether by fate or design, it’s a matter of fact that there’ll be a veritable sea of single men rushing to bars, clubs and local watering holes to try their luck with all the single ladies. In honor of the bachelors among us fighting the good fight, we called on our crack team of dating experts to create a game plan for how to get lucky on this most hallowed lovers’ day. We also invoked the wisdom earned from our worst encounters with the female kind to provide a little insight on how NOT to act if you’re hoping to turn the lust game into a love match. Or how to stop her in her tracks the moment the tryst is over. Whatever works.

If you're into playing your chances with your better half, check out our guide to Gifts For Her That Benefit You.

GET HER: Pay for her drinks, help her with her coat, open the door for her.

It doesn’t matter that she’s a relative stranger, even after two gin and tonics and a tequila shot and all of 20 minutes’ of slurred back and forth. Your mother taught you the same thing ours did: if someone’s kind (/crazy/drunk/desperate) enough to have sex with you, she deserves nothing but your respect.

LOSE HER: Make jokes at her expense, especially if it involves baggage from her past.

Preying on a woman’s insecurities, joking or not, is a surefire way to get canned. Chivalry is alive, thoughtfulness will be rewarded and dicks don’t always get the action they expect. Keep that in mind. Or throw it out the earhole.

GET HER: Compliment her on looking beautiful in a genuine, non-predatory way.

Whether she’ll admit it or not, she dressed that way so a nice, handsome guy with an eye for the details (we’re being optimistic) like you (super optimistic) might take an interest. Girls are used to wading through piles and piles of assholes. They’re everywhere, and the potential to be one exists in every one of us. Stand out as the guy who has his head in the right place. Even if it’s an act.

LOSE HER: Allow a poor esthetic decision to be a reason to put your relationship on the chopping block.

Remember that time she was an autonomous human being with personal agency? Yeah, that time is now. And before she met you. And after she leaves you. She may be sensitive to criticism, but if you’re sensitive enough to a mosquito bite–sized issue like a bum haircut to dish it, prepare to get it.

GET HER: Humor her idea of good conversation, play the sympathy card.

You’ve just met this girl, you’re single and chances are you haven’t gotten laid in a while. Maybe she’s as nervous as you are (admit it) and conversation’s a little rocky. Barring racist tendencies or talk of any noun ending with the suffix “-cide,” you grin and bear it. Act like it’s the best thing you’ve heard since the last Nickelback record came out. And if that fails, manipulate her emotions by playing the sympathy card. That means bringing up your recent (but not TOO recent) terrible breakup, or maybe your (nonexistent?) dead girlfriend. She’s yours.

LOSE HER: Tell her to her face how much her “quirks” annoy you.

So, that time she asked you to fill out a Cosmo relationship quiz and then made you change your answers to make your relationship seem more secure? That’s torture. Telling her it’s torture will ensure your low score on paper is reflected in reality.

GET HER: Make it as much about the journey as the happy ending.

Seriously. Seriously. There’s nothing a single woman loves more than a fun, spontaneous and sexy night out with a new guy. Impress her with your nightlife know-how by bringing her on an adventure that will make your city seem like a whole new one. It’s the classic case of show, don’t tell: don’t talk about all the trouble you’ve gotten into, bring her in on it. Then you’re partners in crime. Who maybe go home and get naked.

LOSE HER: Treat the morning after like the journey’s end.

Hangover blues and morning-after looks can be killers. Acting like a petulant child will ensure you won’t get any looks from her again, even if you’d like to. But if last night’s romance really isn’t ringing true, tell her so and send her on her way. Just treat her like a lady on the way out.


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