A Gentleman's Guide To Being A Successful Wingman

Know this: As a single man, the most important element of your dating repertoire is your wingman. If he fails, you fail. You're only as successful as your friend.

Now, consider this: If your boy was freshly single, and needed someone to put his pistol first and play shotgun, how likely is it that you'd be the one he called?

Commit to being a better friend and master the craft of camaraderie by sharpening the most important skill you can possess—taking one for the team. Brush up on your pointman game with A Gentleman's Guide To Being A Successful Wingman, and kiss your cockblocking days goodbye. Trust us, your friends will thank you later. (And, most importantly, repay you in kind.)

When you accept that the night won't be about you, you instantly become a better wingman. If you're there to assist, you need to lay low like Stockton and don't try to score, so that your boy will be practically guaranteed to (like Malone). 

Why? Because a woman knows when a man is in pursuit. That's why the best wingmen are taken, wifed up, or at least held down by something semi-permanent. A man who already has a woman (or is resigned to not looking for one) can successfully approach a group of women, but if she thinks you're selling something, you've lost.

Instead, work the true wingman angle by shelving your ego and being all about your boy. Go in like you have nothing to lose (because you don't! You have nothing at stake.) and you'll appear nonchalant and confident—just like a taken guy—instantly lowering their guard (and raising their interest).

Boosting your boy's confidence is great, but keeping it real with him is just as crucial. Nothing will stifle his swagger like getting shot down by a girl you knew he had no shot with, or who appeared entirely uninterested.

If he aks that you chat up the model chick in VIP, and he's clearly over-extending himself, you must point him in the direction of a more suitable woman without hurting his pride. "Those VIP girls are always a headache. Plus, we'll end up dropping way too much cash on bottles. How about the cute blonde drinking the beer?"

Congrats, you just avoided watching your man walk into a land mine, and saved yourself the inevitable eye rolling from Mrs. Out-Of-His-League. Win!

This is not your time to shine. Master the art of being unobtrusively entertaining. Turn on the charm to capture the attention of the group, but once your boy enters the picture, fall back.

Levy just enough charisma to maintain the interest of the peripheral ladies (that's why you're there) but not enough to become the object of his desired woman's attention. Remember, you're not trying to win anyone over. You're only trying to warm up the scene, get the crowd ready for the main attraction. You're the opener, he's the headliner.

When your boy has successfully engaged the woman of his fancy, being a wingman becomes less about the approach and more about playing the offensive. It is now your job to prevent her friends from cockblocking your friend.

It's not that women don't want their friends to be happy, they just don't want to feel like left out. Maybe jealously is to blame, but more likely it's just boredom, which is why you now need to get on your One Man Band Man shtick. Be Swizz Beatz.

If you're dealing with a group, be friendly and entertaining. Maybe do double-duty and play wingman for them. The idea here is to have a good time and enjoy their company without creeping. Reassuring them that your friend is a genuinely good guy always helps.

Things become considerably more tricky when it's a one-on-one situation. It's a rare woman who enjoys being left alone in a bar, and it's strict girl code that if one woman is uncomfortable, both will leave. Women can be counted on to adhere to this code with religious tenacity.

Thus, you are left with the grenade, a woman who can detonate with frustration/neglect at any moment, ruining even the most valiant of efforts.

Your course of action? Well, first off, don't treat her like a grenade. If she feels like she's the bad egg you've been ordered to keep warm, she is going to fly the coop. Lame puns and mixed metaphors aside, don't babysit this person! Engage her: dance with her, buy her a drink, ask her questions, and be interested in her because she is a flesh and blood person with feelings and opinions and it won't kill you to be a decent human for a couple hours.

In other words, remember the charm we asked you to tone down before? Now is the time to turn it up!

You've been a selfless wingman all night. You've approached several groups of strange women on your boy's behalf, dialed down your ego, and even pulled some MacGyver moves on a grenade or two. Wingmanship has proved to be your forte, but you can easily lose the props (and the return favors) you're owed in the final round, the one that counts the most.

As the night winds down, as 4 a.m. approaches, you'll reach a crossroads. You'll either continue bomb-sniffing at the after-party, or leave the results of your matchmaking to their own designs. If your boy calls for overtime, don't try to bail on your shift. Follow through until you're off the hook.

Likewise, if young grasshopper is comfortable kicking it on his own, don't overstay your welcome; just quietly bow out.

We hate to conclude this way, but we'd be lying if we left out this fact: Women make superior pick-up pals. One woman can easily chat up another and effortlessly lower the other's guard. Hell, she can even directly address her role as wingwoman to another woman, and still snag your boy an introduction.

A wingwoman's effectiveness boils down to two things:

1. Women will inherently trust a strange woman over a strange man. If two women hit it off, and the wingwoman vouches for the guy, he's been given a shot. No questions asked. Just enjoy the opportunity.

2. Aside from another woman's seal of approval, approaching a female with another woman may incite her jealously, or ignite her competitive nature, both of which will make you appear more desirable.

So, when in doubt of your ability to take one for the team, have an attractive, friendly woman in tow. Chances are, she'll be twice as effective and with half the effort. Sorry, guys.