Guy's Guy™
Guys' Guy's Guides™

No Wingman, No Problem


Dating in 2017 can be tricky, but the game of love hasn’t really changed all that much. Despite the plethora of online dating sites and apps, swiping left and right making a one-on-one connection still requires a Guy’s Guy to step up and seal the deal on his own.

And that’s the way it should be. Your best bud can be a good sounding board on the front lines at the bar during your hunt for female companionship, but when all is said and done, does a Guy’s Guy really need another dude to help him chat up and connect with a lady? I think not.

The concept of deploying a wingman emerged over the past few decades. Maybe it began when the online dating technology nudged its way into the mainstream. No longer did a guy have to man up and approach a lady face to face with the real possibility of flat-out rejection. Instead, young bucks can sit at home in their tighty-whiteys plinking on their keyboard and chirping with attractive women on one of the many dating sites and apps. Maybe guys have gotten lazy and soft because they don’t have to put themselves on the line. And as a result, some younger fellas may have fallen behind their older male predecessors in the art of charm and small talk. So on those occasions when they head into the night out looking for love, they recruit a friend to help break the ice with the women. No judging, mind you.  But if this makes sense, read on…

Now, there is nothing wrong with going out with your buds for a few brews with the possibility of meeting some ladies, but ultimately, there are certain things a man needs to do on his own. One of them is stepping up and forging a face-to-face connection with a woman. You don’t need to be rubbing shoulders with your best bud to make that happen. Sure, there are a few advantages to bringing along a friend when trying to meet women. You won’t risk being seen as the creepy guy who is out by himself. And, your wingman might help grease the wheels during those often-awkward first exchanges with a strange woman and her friends. But, when having a wingman on board can also crate a few unwanted problems? What if he thinks you’re his wingman and you find yourselves both interested in that same cute blonde? Or what if he’s not looking, but the lady you’ve got your eyes on is more interested in him? Or, maybe he’s better looking, has more bank, or a better rap than you. Then you are competing with your wingman. Not good, amigo. And, even if he’s in a relationship and not looking, he’s still human. And that means he might be taken with the same lady that caught your attention. So, on the surface it may appear that recruiting a wingman has some benefits. But as you can see, there are a number of pitfalls that come with the program. 

Now you may be thinking, “Oh, what about a female wingman or wing woman”?  That’s a better option, but do you really want to deal with filtering your horn doggie passions through the lens of a woman friend who may not like the ladies you are chatting up? And what if they don’t get along? Or what if your wing woman only accompanied you to either check out your game or maybe she even has her eyes set on you? It’s gets complicated.

Amigos, the news is not so bad.  There are plenty of opportunities to meet women without the help of a wingman. You can meet women at work, through friends, at clubs or organizations, at the gym (if you keep your cool), in a class, at a wedding or a party, at Whole Foods, or the museum, all by just by being yourself. Nothing beats the old-fashioned, organic way of chatting up women anywhere, anytime, any place. No pick up lines, no games, and no bullshit necessary. Just be your authentic self and approach a woman confidently with an observation, an open-ended question, or a smile and, “Hi, I’m Jason.” Believe me, just being you works. Once you get comfortable in your own skin, you can talk to any woman. Not every woman will respond the way you want them to, but so what? It’s a game, and when a lady expresses some interest, then it’s on you to keep things going. And, you know what? That’s a Guy’s Guy game and one you can win. So, although it’s comforting having a wingman at your side, you’ll be ahead of the game and a leader of the pack if you go it alone. Vamanos, amigos!

This week’s GUY’S GUY OF THE WEEK is Vince Vaughn. Here is a guy who plays a role like he owns it. He knows his game and can talk to any woman any time, anywhere. And, that my friend is money.