The Dos and Don’ts of Trying to Pick Someone Up on V-Day

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Valentine’s Day is famously unkind. Even the couples it’s intended for feel the pressure. But just like weddings, it’s an occasion when people are actively searching for some validating human intercourse interaction and that means it’s a better day than most to put yourself out there. Sure, the pick-up might be tinged with desperation (yours or your target’s), but wait—what’s that sound? That is the sound of opportunity knocking.

A portion of the dating population will decide to stay home and out of V-day’s way, but the rest of us will be out trying to make the day worthwhile. A bar, a coffee shop or the dog park would be good bets, but the ice cream aisle might work too. Once you’re there, have a lead-in ready.

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Okay, this is always the hard part. But today is different because people are generally going to be more receptive to making new connections as long as you don’t approach groups of girls clearly intent on having a boy-free, no-reminders-of-romance evening. You can identify those girls easily because they will not be making eye contact and possibly near a pile of gifts they bought each other.

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Feel free to mention that it’s Valentine’s Day with something innocuous like, “Happy Valentine’s Day!” or a comment on the candy or decorations nearby–just don’t go overboard with bitter humor. Even a simple compliment would be a great way to break the ice on a day when people are feeling vulnerable. Tell a girl you like her shoes, or a guy that his shirt is nice.

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Under no circumstances should you say the following:
“Can I pinch you for not wearing pink?”
“So. Alone on Valentine’s Day, huh?”
“How about I St. Valentine’s Day Massacre that ass?”

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Remember not to push your luck. A lot of people could use a self-esteem boost and will be open to some innocent flirting and possibly more–how much more depends on the person. Valentine’s Day pick-ups are like Vegas: What happens there might need to stay there.

Nikki Metzgar is a writer from Texas. She thinks the best first dates don’t include sit down dinners, but can’t help but be impressed by flowers. @nikkimetz

See also:

3 Ways To Make Your Valentine’s Date Actually Romantic
5 Things I Learned About Sex From Rap Music
10 Signs You Need To Go On A date