wingman
The other day I was out with a newly single friend who wanted to talk a bit about how we could potentially “wingman” for each other.

“So you mean that we would go out and then randomly talk to girls together in hopes that, at the end of the night, one or both of us will get to go home with one of the girls that we spoke to?” I asked.

“Well, yeah. Except both of us would never go home with one of the girls we were talking to. I love you but…”

“I know, I know. We must avoid The Devil’s Threesome.”*

That’s pretty much rule number one.

Here are some additional wingman guidelines we came up with:

Keep your friend presentable. If one of you is wearing something wack, make it known before you leave for the night. It can be tempting to want to look better than your friend, but the two of you are in this together, at least at the outset.

Don’t crowd a solo woman. If there is one woman and your friend is like “I would like very much to put my tongue in her mouth,” don’t go with him to talk to her. This is not only confusing, but also vaguely creepy. And your friend is going to be ultra-pissed if you’re both talking to her and she takes a liking to you instead.

Be brave. The two of you need to just go talk to them. Think of it this way: if it doesn’t work out, what did you lose? Not a damn thing. Chances are probably pretty good that, depending on where it is you are, you will never see them again anyway. And if you do, who cares? Keep in mind that it’s easier to talk with people when you already have a friend with you to help ease the conversation along. Strength in numbers, fellas.

Support each other and shrug off rejection. Allowing yourselves to get upset when women make it clear there is zero interest is not going to do you any good at all. When it happens, make sure you tell your friend he is smart, beautiful and important, and then move on to the next group of fillies.

Gather intel for each other. If one of you is making inroads, try to find out things about her from her friend(s). Then, when the ladies inevitably go to the restroom together, you can conduct a quick debrief.

Don’t make jokes about your boy. If you’re anything like my friends and me, your favorite thing to do is make fun of one another. Life is more fun when you’re laughing, right? Well, try to find things to talk about other than your friend’s quirks or shortcomings. It’s probably not going to do him many favors, and the woman he’s attempting to woo will find out plenty of them anyway if she sticks around long enough.

Don’t oversell your boy. Don’t rip on him, but don’t spend a bunch of breath singing his praises, either. Bromances are an important part of life, but keep the man-on-man non-sexual love to yourselves, at least during a first meeting.

Be open to taking one for the team, but don’t forget about it when one of you does. I was watching this porn video the other day (surprise, surprise) where these college roommates had two girls over and one of them agreed to get fresh with a woman he didn’t find attractive. This equates to martyrdom in the world of wingmanning, and if one of you takes one for the team you are owed until the other balances and restores justice.

When the time is right, isolate elegantly and quickly. If it looks like your friend is potentially going to score, leave him with the woman at the appropriate time. Try your best not to broadcast that you’re leaving intentionally so he can be alone with her. The two of you may want to discuss a plan for a one-man exodus, actually, if the opportunity presents itself.

*Devil’s Threesome = Two dudes, one woman.