The 5 Principles Of Being A Wingman

The 5 Principles Of Being A Wingman

Your buddy? Yeah, he’s in a slump. Maybe he just got out of a relationship, maybe it’s the tail-end of cuffing season and he hasn’t locked anything down for the winter, or maybe he’s just a total doorknob with no social awareness. Either way, one thing is apparent: you need to take him out and get him back in the mix.

Believe it or not, I’ve been there, guys. Yeah, I had a monster December last year, but don’t let that overshadow the cold streak I was on between Labor Day and The Night Before Thanksgiving. But once the clock struck twelve and it was officially Turkey Day? I was first-base’ing all night with a cutie only to spend the entirety of Thanksgiving watching the Lions beat the hell out of the Bears with my boy, Tube Socks.

Tube Socks was a revelation that weekend. After all, he had a five-day weekend, no work obligations, and his girlfriend was spending time with her family (don’t worry, we all love her so he didn’t do anything wrong), so he could wheel and deal as he pleased. His mindset? Be the best wingman possible. And that’s exactly what he did. If you looked over your shoulder, he was buttering up biscuits and getting them warm for all of us to go talk to. And if we got burned on the first batch? He was pre-heating the oven for more.

See, Tube Socks had all the tools to be an A1 wingman and I never even realized it. It was kind of like when Tiger Woods won The Masters in 1997: we all knew he had the talent, but we had never seen him revel in his greatness and get the result he was looking for. So what choice was I given when I wanted to share his wingman knowledge with the masses? I asked him exactly what his principles of being a top wingman are.

I. Be really enthusiastic. Make her realize that your boy’s friends are awesome to be around.

A great man once said, “It is your attitude, not your aptitude, that determines your altitude.” If you put out a center-of-attention, peacocking vibe? People are going to notice. And if you make a group of girls realize that your boy only chills with a group full of filets in a bar full of side salads? It’s game over before the puck even drops. Sure, every other guy in the bar will hate your group of friends because you’re commanding attention, but no one ever got a girl because he was sitting against the wall with a thumb up his ass.

II. Give space and talk to the girl’s friends a lot. That way her friends are entertained and then she has to talk to your boy.

Oh, everyone else has paired off in some casual bar-side conversation? Perfect. That means the apple of your boy’s eye has no other choice but to engage with him. By using the process of elimination and ensuring all of her friends are having a blast, she’d have to be a selfish little brat to deny talking to your friend, no matter how cold of a streak he’s in. No one wants to rain on everyone’s parade. And if she does? She ain’t worth the time of day.

III. Casually bring up the story about that one time your boy did something awesome (without being too over the top that you’re clearly trying too hard to give him a boost).

“Remember that hole-in-one you got to give us a 2-stroke lead in the club championship?”
“Your dad still has that lake house, yeah?”
“You lead your team in goals in your last season playing club hockey, right?”
“Michigan Law is hard to get into, but none of us had any doubts about you getting in.”
“It’s crazy how only gorgeous blondes love you. I’ll never understand it.”

The properly placed compliment, quip, or remark yields more gains than any of us can even fathom. It’s like poison ivy. Once it appears, it ain’t goin’ away.

IV. Encourage the girl (and her friends) to do something fun in the future.

The night you’re out? You’re just settin’ up. No one said a wingman had to watch his crew land girls that night. After all, no one wants to be known as the asshole group of dudes that just hit it and quit it. But this strategy? It positions you perfectly for a future date or night out.

“Oh, what are you doing Thursday?” Boom, you’re at happy hour on Thursday where you have the struggler say, “We’re heading to the Cubs game on Saturday because the weather is supposed to be awesome and the beers will be a-flowin’.” Stop the fight, because now you’ve got plans for days (and they know you’ll be paying for everything).

V. Be cool, but don’t be a cool fool.

Don’t be obvious. If it’s completely evident that you’re just trying to be the best wingman this side of the Mississippi? Everyone’ll see right through you, and that’s just devastating for the collective group. Flying under the radar ensures that you and your boy know that you’re being an incredible wingman, but it leaves the desired party in a state of wonderment thinking, “Ugh, these guys are so much fun to be around!” Being seamless is essential.

And if all else fails? Hey, at least you’ve got a killer best friend.

Image via YouTube

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Will deFries (Twitter / Instagram) is a Senior Writer at Grandex and the world's foremost authority on Sunday Scaries (Twitter / Instagram). Email me at

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