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A good wingman or wingwoman (‘wingman’ is a gender-neutral term, like ‘ombudsman’) makes the tricky process of befriending strangers smooth and easy. A wingman is a self-sacrificing person who does whatever they can do help their point-friend score by gassing them up and making sure everyone is comfortable.

For a point-and-wing combo going out on Valentine’s Day, the wingman’s job is even trickier and more important, as the night can be loaded with high expectations and emotional pitfalls, especially if someone recently got out of a relationship. This is a guide to staying cool, making connections, and having a good time as a wingman on Valentine’s Day.

1. Tip well

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It’s always important to tip well, but it’s extra-important on holidays. The bartender would rather spend Valentine’s Day with their significant other than at work, serving all these happy couples. Acknowledge their sacrifice with money. Plus, tipping well helps you get on the bartender’s good side, and being on the bartender’s good side makes you look cool. Finally, people notice how others treat service staff, and being rude or stingy is almost always a turn-off.

2. Boost your buddy’s confidence

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If your point just got out of a relationship, he or she might be sad, unsure, or rusty at the talking-to-strangers game. It’s the wingman’s job to not just make your friend look cool to the people you’ll be talking to, but to themselves. This means encouraging them about their looks and value and style, pumping them up to approach someone, and making sure they’re dressed well and properly groomed.

3. Make your buddy look good, but not too good


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Your main job is to talk up your friend to the woman he likes (from this point forward, we’ll be using “he” pronouns for simplicity’s sake). But don’t go overboard. If your testimonial feels phony or forced, she’ll sense that and flee. Don’t lie or exaggerate about how your friend is a humanitarian underwear model billionaire, but if your friend has an interesting job or funny story, prompt him to talk about it. If you observe that the two of them have something in common, verbalize that connection. It’s more about offering corroborating evidence than giving a hard sell. Never tear him down or undermine him, even in a joking way. If he’s your friend, it shouldn’t be hard to say something nice about him.

4. Don’t drink too much

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Have fun, but don’t overdo it. If you get sloppy and incoherent, you will compromise your effectiveness as a wingman. Your friend is being judged on the company he keeps. If he can’t trust you to keep it together, how will you build trust with the woman he’s talking to? How will he seal the deal when he has to take care of you?

5. Create verbal frames

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This is a neat bit of social science: people subconsciously respond to the implied context of what’s being said. If you address your friend and the woman he likes as a unit (“you all should come my lake house this weekend”), she’ll consider the possibility of herself and your friend as a couple.

6. Don’t make a big deal out of the fact that it’s Valentine’s Day

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The holiday might make going out to meet people feel pressurized, like every interaction is an audition for a long-term relationship. But don’t stress it! Everybody else there is hanging out on Valentine’s Day, too. The holiday gives you a conversational in to play with. You can draw attention to the fact that it’s Valentine’s Day while simultaneously implying that it ain’t no thing to you.

7. Relax!

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Your buddy may feel funny about Valentine’s Day; it’s up to you to set the tone that you’re just having fun. Don’t create an elaborate plan and have expectations that it’ll go perfectly. Just sit back and let the night unfold. Be natural and say what comes to mind. If you’re cool, people will naturally be drawn to you. Take a deep breath, crack a smile, look your friend in the eye, and say, “you got this.”

via dewutang