How to wing: 4 crucial tips to be a good wing man

This is a Bonus chapter from Kickassery (updated for the blog).

Rule #1: A good wingman is your ride or die homie.

What does this look like?  It’s well-known wing etiquette that you wing the guy who speaks to the girl first.  But it goes beyond that.

It means you pay attention if your wing is speaking, that you never cut him out of a conversation by turning your back to him, and that you consistently ask yourself “How can I help my wing?”

This is TOUGH for most dudes.  They are nervous about speaking to strangers, even though they’d obviously love to be talking to cute girls. When they see their buddy speaking to one, they pounce.  They get in there and start trying to win the girl over.  Before long it devolves into a struggle between the friends for air time.  The girls sense their desperation and wander off.

Your wingman IS NOT just someone you walk into a bar with before stabbing him in the back.  He IS NOT a competitor.  If that’s how you roll, you’re killing your long-term success.

A much more effective way is to think of you and your wing as a unit.  Economics / Game Theory bears this out.  If you both independantly pursue your selfish interests, you might feel like you’re optimizing your outcome . . . but if you cooperate and can count on your wing to do the same, you both wind up better off (think of the prisoners who rat on one another).

Don’t be the friends who rat on one another

Ben and I refer to ourselves as a “singularity.”  We are constantly optimizing for the happiness of the two of us as a unit.  We never, ever compete over a girl.  No exceptions.  Sometimes even if I speak to a girl first, if he likes her more, I back off.  It doesn’t matter if that means he gets three girls in a row.  We truly think “Who will this make happiest?”  In the long run it makes us both MEGA happy.

So practice generosity.  Start pulling your wing into groups you’ve opened.  Let him take the pretty one if she’s more his type.  Talk him up like whoa (more on this in rule #4).  It comes back to you in spades.

Remember: If you can’t be generous with your wing, you’re better off going out along because you’re just going to hurt one another.

Rule #2: Help each other get in state

People HATE going out alone because they don’t know what to do with themselves.  They wander the bar or club like a shark, never stopping to actually interact with people.

Unfortunately when you add a wing to the mix, most guys keep the sharking going.  The only difference is, instead of wandering with their feet, they wander with their eyes.  You’ve seen it a million times.  Two guys leaning against the wall, unsmiling, beer in hand, not speaking to one another as they scope out the bar in between sips of Miller Lite.

That’s garbage.

The coolest spot in the bar is the space between your eyes and your wingman’s eyes.  So when not speaking to anyone else, focus there.  Look at each other and talk.  Laugh.  Clap one another on the shoulder.  Smile wide for no reason.  Make a game of it.  Jump up and down.  Shake each other to get your bodies moving.

More on this in another post, but the key is this: your state is the single most important factor in your ability to attract women on any given night.  The best way to get into a good state is to change your physiology and your focus.  So uncross your wing’s arms, pull his hands out of his pockets, and FORCE HIM to smile, shout, and laugh.  You’re doing him THE BEST favor possible.

Plus, you lose nothing by not sharking with your eyes.  You can easily see what’s happening around you with your peripheral vision.  You are totally aware of what’s going on behind your wing’s back and vice versa.  And you’ll notice that girls draw closer to the two guys in the room who are laughing, shouting, and jumping around.

Rule #3: Communicate with your wing

Your wing walks into a group of 3 pretty girls and strikes up conversation.  How do you know if you should help or let him hang for a while?  You need a way to ask him.

Ben and I love to play around at this.  When one of us walks up to the other in a group, we’ll yell, “What up Shaq?”  (Yeah, like Shaquille O’Neal).  The other will then answer in a sentence that includes one of three words:

  • “What up Kobe?”:  “I got this.”
  • “What up Steve Nash?”:  “I could use an assist.”
  • “What up Shawn Bradley?”:  “I’m just having fun and am not trying to hook up with these girls.”

It’s goofy as all hell, but super helpful.  You’ll be amazed by how your wing’s tastes differ from yours.  And it is really nice when you find out he is uninterested in a girl you are really attracted to.

If you ever need to clarify, do so.  Seriously, just walk up to your wing, lean in and ask, “Who do you like?”  He can answer right back.  Most bars and clubs are so loud no one has a shot at hearing what you’re saying.  And no one asks what you were saying so long as you are not weird and overly secretive about it.

Rule #4: When asked, help like crazy

When your wing says “Steve Nash,” it’s time to go to town.  Your goal is basically to SHOUT the coolest things about your buddy.  It is remarkable how much bragging you can get away with as the friend.

I will literally grab girls’ hands and put them on Ben’s abs.  I tell them to swoon over his 6-pack because it is as deep as the Marianas Trench.  I tell them how he is my bodyguard since he is an MMA fighter and I am a giant pussy when it comes to fighting.  He will ask girls how they know me, then immediately launch into how I am an amazing guitarist/singer.  We both congratulate girls on finding the coolest guy in the bar (the other one).  We both complain about living with one another since the other is so good at sex and it can make it impossible to sleep through the noise when he has someone over.

The point is this: find out your wingman’s best traits and bring them up like an obnoxiously proud father.

Later, if we see a girl the other is interested in outside of conversation, we basically tell the girl how bad she needs to hook up with the other.  Like, fervently.  I know it may read weird, but it works.

We were out at a costume party one night (story for another day) and Ben had seen a girl he thought was cute.  They talked and danced for a bit, but when he went for the kiss she played coy.  Ben got bored and wandered off and found someone else to kiss.  Still, when I bumped into her again, this is what happened:

Her:  Hey.
Me:  Oh god you are so boring.
Her:  What?
Me:  I saw you play hard to get with my friend.  That is lame as shit.
Her:  No I wasn’t!  I kissed him!
Me:   Yeah like this (makes kissy face but plays hard to get).  You blew that one.  
Her:  Haha well what is so great about him that I should kiss him?
Me:  First off he will never tell you this, but he is by far the coolest guy in here and awesome in the sack.  I know.  We share a wall and I have to listen.
Her:  Well, where is he?
Me:  Probably making out with someone else.  You lost him.  You were so boring.  It’s over for you.  You had a shot at the title and you fucking blew it.
Her:  Well he just wants to have sex.  He does this with all the girls I bet.
Me:  Listen there are a lot of people in this world I wouldn’t say this about.  In fact there is probably only one person I would say this about.  But he is the most genuine, hot, authentic, rich, honest person on the planet and YOU RUINED IT!
Her:  You’re just saying that because you’re his friend.
Me:  No he is my friend because he is awesome.
Her:  [hunts Ben down to go make out with him.]

The fastest way to get good with people is by having someone to go with on the journey.  That dude is your wing.  His presence will hold your to a higher standard and make the sometimes terrifying process much more fun.  Plus, if you do it right, you’ll do each other more favors than you can imagine.  Learn how to be a good wing man and TREAT HIM WELL!

  • Be generous.  It comes back to you.
  • Help him have fun and look cool.
  • Communicate.  You need to be on the same page.
  • Go over the top in praise for one him.  You are his best advocate and he is yours.

Boom shaklaka!


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