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6 Ways to Be the Best Wingman Ever

November 23, 2009
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I asked a friend of mine, Eric (who is happily dating right now), to write a special guest entry about how to be a great wingman. There’s some great advice below, so take heed.

  1. Pick the pilot, and stick with it. Before you step out for the night, you and your buddy need to know exactly who you are “wingmanning” for the night. It doesn’t work both ways where your buddy can “wingman” you for the night and vice versa. That’s because there’s no off/on switch for a true wingman. You need to be focused entering the night, and maintain your wingmanship until the bitter end.
  2. Leave the awkwards home alone. Wingmanning is a sweet and delicate science which requires precision at the most subtle of moments. That’s why you need to make sure you give your buddy the best chance of succeeding before you roll out for the night. That means leaving all of his (and your) awkward friends for the night home alone. You know what I’m talking about: it’s the guy who still hasn’t gotten laid at the age of 27, the guy who has about 30 seconds to talk to a girl before freaking her out, the guy who dresses like his mom just went nuts at the “Back to School Sale” at Macy’s. It’s the guy who says he wants to go out but you know deep down inside he’s all about staying at home and riding the elliptical while watching some softcore porn. It’s the guy who you once thought was asexual until you learned that he played with himself in the backseat of your car on a long roadtrip. Leave him at home. Don’t take him. It will ruin everyone’s night and he’ll spend the rest of the night talking about how he talked to a girl for those 30 seconds.
  3. Make him put his money where his mouth is. It’s not the wingman’s job to approach the women. No sir. If your buddy wants to score for the night, he better damn well have the gusto to approach. And that’s where the dollar bills come in. You see, lots of guys talk the talk but can’t walk the walk. You and your buddy may be all geeked up to go hit on some lovely ladies for the night, but if he can’t approach, then you never even get to testing your wingmanning abilities. Get your buddy to give you $50 in cash before you head out. The deal? He gets it back as long as he approaches three women. It’s a win-win situation.
  4. Take the bullet regardless of how big it is. As a wingman, you must rid your expectations of picking up an attractive woman. The night is about your buddy and his quest to conquer the opposite sex, not about you and your libido. That’s why when you approach a group of girls, whether it be two, three or four, you must pick the ugly one and entertain her. Every group has one. There’s always that one girl that sticks out like a sore thumb. You can spot her from twenty feet away: she’ll be looking around awkwardly, playing with her hair, potentially staring at the ground trying not to create too much attention while failing to do so at the same time. She, my friend, is your job for the night. If you have to listen to her talk about her cat “Muffin” and her new Iphone apps so be it. You love cats for the night and her Iphone apps are amazing. The more you keep her engaged, the better chance your buddy has of picking up the target. If she disengages, you can kiss the rest of the group (and your buddy’s chances) goodbye.
  5. Embellish. For the night, your buddy is the greatest guy to walk the earth. He’s got a hint of the rugged guy in the Levi’s commercial blended with the smooth, suave guy in the Disarrono ads mixed with the dude with the twelvepack selling the abrollers. Even if you know he isn’t that guy, he’s that guy for that night. Talk him up. Make sure you know that the girl he’s talking to thinks she’s talking to the King Kong of club life. The more you build his social value in a group conversation, the better chance he has.
  6. Never leave your wingman. You’re tired. It’s 2:00 AM, your leg hurts from playing flag football earlier in the day and you want to get to bed. You got Mrs. Ugly talking her head off at this point and your buddy still has his girl engaged. Don’t you dare ditch out. Give him a signal. Let him know you’re running low on juice. But don’t for a second think about leaving without him at the bare minimum getting a number. Leave it to him to close the night with an offer to take the party elsewhere or seal it with some digits. Either way, let him control his own destiny. It’s his night, not yours.
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8 Comments leave one →
  1. Dionne permalink
    November 23, 2009 11:32 am

    That’s freakin’ hilarious! I luv it! Eric must be the best wingman ever! Two thumbs up my friend.

  2. T-Mac permalink
    November 23, 2009 1:58 pm

    Aside from 2 Halloween’s ago when we all dressed as wingmen, I have zero practice being a wingman. It sounds challenging. My question for the great Eric (or Jamey) is what the wingman does once he has engaged the unattractive group member in conversation and the “buddy” has acquired a phone number, etc. How does the wingman disengage without the unattractive friend realizing that she has been the victim of a winging and telling her attractive friend, thus negating the wing effort?

    • November 23, 2009 2:25 pm

      I think the key is that in Eric’s system, there is no victim. Everyone wins. The less attractive girl in the group who doesn’t usually get hit on gets some much-desired attention, the wingman himself has some fun flirting with full knowledge that he’s not trying to take anything to the next level (so he can’t lose), and the “pilot” gets to chat with a cute girl for a while (with the potential for more to happen).

    • Eric permalink
      November 23, 2009 2:35 pm

      I hate to say it, but I think the unattractive female knows when her time is up. Everybody is cognizant of the “game” that is being played, they just get upset when it’s not being played right. So when your buddy gets the number and he’s ready to disengage, then its pretty much game over. You can just tell her it was nice to meet her and go on your way.

      • T-Mac permalink
        November 23, 2009 4:11 pm

        Female readers–I’d love to hear from you. Is this true? Have you ever had two guys approach you and a friend to get your number, and was one of the guys too good looking for your friend, but talked to her anyway? Did both of you realize that the goal was just to get your number (not hers) and move on? If so, was your friend OK with it because she got to talk to the wingman for awhile?

        • Dionne permalink
          November 23, 2009 9:40 pm

          I don’t think women are going to admit if they’ve been “wingmanned” so good luck with that…lol.

  3. Dionne permalink
    November 23, 2009 2:06 pm

    Good point! I want to hear this answer….Eric…Jamey?????

  4. Joe S permalink
    November 23, 2009 4:44 pm

    Eric is a great man and a great wingman. Heed his advice! He knows his stuff.

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