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Finding A Quality Wingman Is Harder Than Finding A Girlfriend

Finding A Quality Wingman Is Harder Than Finding A Girlfriend

So, back in July, I got dumped. Don’t feel sorry for me, I don’t want your pity. I was a dog-shit boyfriend who had it coming. Obviously, it sucked at the time and still does to some degree but life goes on and blah, blah, insert an uplifting quote from Instagram here.

There are a lot of adjustments that one has to make when they’re newly single: not having someone to text throughout your day, having to get back in shape because you never lost your relationship weight, having to unfollow dog accounts on Instagram because you have no one to send the pictures to anymore.

For me, I basically have to learn what it’s like to be single in your 20s for the first time. At the age of 26, no less. Friends, I’ve been in two back-to-back relationships over the last six years. While most of my friends were all out chasing any girl who didn’t immediately scoff at their mere presence, I was the relationship guy who would leave the bar early with his significant other to polish off some Chinese food with an Office rerun playing in the background. Needless to say, I have some learning to do since I’m essentially a rookie of the game.

While 26 isn’t too old to be reintroduced to single life after an extended leave of absence, it certainly comes with a learning curve. The quickest observation that I’ve made so far though is that there are so many people who are ready and willing to be your wingman when you’re the single guy, but unfortunately, most of them are lacking and it’s annoying as shit. Whether that person is your longtime single buddy who is foaming at the mouth to live his own personal version of Wedding Crashers with his new partner in crime or it’s your brother who likes to play the “Haaaavvvee you met Kevin?!?!” game that barely even worked on How I Met Your Mother. They may have the best of intentions, for the most part, but the chances of them being an aid to you making a connection with a girl are slimmer than my chances of not drinking alone on a weeknight.

Unless you and your buddy have the charisma of McConaughey, coupled with the looks of – *Google’s “Hottest Dudes of 2017”* – well, McConaughey, you’re basically shit out of luck from the jump. If you approach a group of girls but then act too passive you’ll just come off desperate and sad. Or if your buddy, and hopefully not you, is the type who believes the babble spewed in Pick-Up Artist books then you’ll have girls reaching for their mace before they’re halfway through those vodka-sodas that he bought for them before you even walked over. Yes, your friend is a creep and you should probably ditch him altogether, but I won’t tell you how to live your life.

Some will argue that guy’s in relationships make the best wingmen because they don’t have to worry about getting other girls. That couldn’t be further from the truth. When I was in a relationship, I believed this to be true as well. Hell, I even thought I was the best wingman in my group. Looking back on it, I couldn’t have been more wrong. My approach was to essentially make an ass out of myself enough so that it would make my friends look better. While that worked sparingly, it usually just turned girls away because I undoubtedly took it too far, something that I tend to often do. Even if your relationship guy isn’t as big of an idiot as I am, chances are that he only cares about getting loaded and entertaining himself while he’s out because at the end of the night he has someone to go home to. Also, he’s still a dick just like the rest of you.

In my opinion, the best bet at finding anything relatively close to a wingman is enlisting the help of your female friends that don’t hate you. While they still won’t be much more of a help than the group of degenerates that you call friends when it comes to approaching girls at bars, they’ll at least be willing to introduce you to girls they know from work or through other friends that they hide from you all. As a single guy, there are few bigger advantages than having a female cosigner. It’ll cut your potential creep factor down and you just have to prove the rest. Granted, you can only utilize this strategy if you’re looking for a girlfriend or are at least willing to casually date someone. I have a close female friend who has tried this for me twice and I had to turn it down because I don’t want anything remotely close to a girlfriend and the last thing I need is to have one more girl in this world hate me for not calling her friend back.

Maybe I sound a bit pessimistic or like I don’t know what I’m talking about. Which could be true seeing as I’m still learning my way through this new experience. Truth be told, I’d love to be proven wrong. Have someone who you know will always be in your corner sounds lovely. In fact, I think I’ll accept applications from anyone willing to prove me wrong, I’ll pay you handsomely in Jameson shots. But until then, I think I’m going lone wolf unless I decide I want a girlfriend soon (HA!) and decide to text my friend asking, “So how about your coworker?”

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Kevin Caulfield

Chicago based stand up comedian and writer. Perpetually taking it too far and apologizing for it

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