Sometimes your Best Wingman is a Wingwoman

“When men and women agree, it is only in their conclusions; their reasons are always different.” – George Santayana

Any man or woman who frequents the single scene, especially the more treacherous bar stage, can tell you what a daunting challenge it is. Between the crowds and the self-judgmental nerves you will have right before trying to meet someone, this creates an environment where drinking is such an integral part of the social ritual just to overcome the fact that you place yourself in such a vulnerable situation. For group support and to avoid the creepy and/or desperate vibe that accompanies all lonely men and women hanging out in a bar, most people rely on having a wingman or a wingwoman respectively.

Wing·man (wiNGˌmən) noun: Wingman; plural noun: wingmen

  1. a pilot whose aircraft is positioned behind and outside the leading aircraft in a formation.
  2. a person who will offer support advice to a friend while dealing with potential partners.

We see them all the time, pairs of men and pairs of women hanging out like hunters in clubs that survey the area for possible encounters. These duos keep each other company, shooting the breeze till an appropriate prospect catches their eye. The wingman will help the gentleman get close to the lady, either by striking up the initial conversation, or by distracting the woman’s friends. The wingwoman will usually assist the lady in avoiding the attention of undesirable men. That is the social norm, guys with guys and ladies with ladies – I guess some things from Kindergarten never change.

I have actually read several articles telling men that his wingman should be another man, because that’s how it should be. They actually mention that you, as a man, should avoid being accompanied by a woman when looking for prospective partners, as it will scare off other women – really? If the intention is to find a lady with whom to enjoy her company, why do we focus on the gender separation? To me, that sounds like the old elementary school dances, boys with boys, and girls with girls, till they get together. Gentlemen, let me make one thing clear, a wingwoman will trump a wingman every single time and here’s why:

1. The fact that you are able to hang out with a woman says a lot about you.

This is a subject most men will usually overlook. How do you expect to strike up a conversation with a lady if you can’t even have a woman as a friend? The fact that you are able to hang out with a woman without it being a date says a lot about you as a man. It proves, at least to a certain degree, how you are not some creepy “nice guy” and how you are able to relate to a woman without hitting on her. This alone places you miles ahead most men.

Also, “hanging out” with a woman makes other women realize that you are not necessarily a threat. As you spend some time with them without ulterior motives, you will get to know them. You will end up getting comfortable around the opposite sex and will realize they are not these conniving creatures some men try to make them out to be. You will realize we are not that different if you stop being such a jerk to them.

2. It’s easier for a woman to approach another woman.

Part of the duties of the wingman is to get you past the initial challenge of approaching a woman. Think of how easy it is for you, as a man, to talk to any other guy. Unless you are at the urinal, it’s pretty easy. (Note: Don’t try to talk to another guy at the urinal. That’s just creepy.) Same thing with women. (Not sure about women striking conversations in the bathroom. You will have to ask a woman about that.)

3. You will realize how wrong “Men don’t understand women. Women understand women and they hate each other” is.

Let me start with the following two clarifications. First, any man who says he understands women is lying. Second, women don’t hate each other, they are just as competitive as men. The funny thing is the more you look at each other, outside the stupidity that society forces on us, men and women aren’t that different, but it’s that social stupidity that confuses men and women alike. Having a woman in this environment helps you get some perspective and decipher some of the social queues that women have.

4. You get a front row seat to the advantages and disadvantages that women deal with every time they go out.

Another advantage of hanging out with a lady, as her friend, is you will get more than a couple free drinks. Way too many idiots think they can impress women by buying them off with drinks. These same fools will think that if they are cool with you, they will automatically be cool with her, assuming your loyalty is for sale.

Here is where you start learning what women deal with, the good and the bad. More than once you will have to stand up to guys who don’t understand when your wingwoman says “Not interested.” More than once you will have to be her “boyfriend” as you get a front row seat to every catcall, every cheap line, and every unwarranted advance. If anything, you will learn what not to do.

“It’s not about the Guy you used to be, but the Gentleman you’ve become.” - Being Caballero - Contributor to The Good Men Project , MNSWR Magazine , and Gentlemenhood . Architect, Writer, Speaker, Gentleman Coach, and Advisory board member to the National Council on Women and Girls and the National Council on Men and Boys .

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