The Wingman

I learned the hard way that when it comes to being a wingman, less is more.

By Cesar Idrobo for Five O’ Clock, a Harry’s Magazine

I always prided myself on being a pretty good wingman. But it wasn’t until I heard my friend Tyler say: “Oh, shit! Oh, shit! Oh, shit!” that I found out just how good I am.

Let me back up a bit. Tyler has an obsession with Latin women, and I come from Colombia. Tyler is an all-American kind of guy, but he can be a little shy at first. So, when I meet girls on campus who’ve come to study from South or Central America, I use our common ground as an intro to a conversation and then I do my best to send them Tyler’s way.

When Tyler is throwing a party, for instance, I can say: “Hey, a buddy of mine is having a party at his place this Saturday night. He makes great drinks. You ought to come by.”

Sometimes Tyler becomes smitten with a particularly beautiful woman, and when he mentions her to me I’ll invite her over. There’s never any pressure, and it’s all very relaxed.

Well, it was relaxed — until one night.

There was this gorgeous Venezuelan who caught Tyler’s eye from afar. I told her about his party and she said: “Okay, I’ll see if I can make it,” in a tone of voice that told me she didn’t want to disappoint me and was trying to be nice, but that there was no way she was coming.

Better ask someone else, I figured. The next girl I told about Tyler and his party was from Panama, and she had a really strong personality. When she said: “I’m not sure I can be there that night,” I figured there was no chance.

So I moved on to another. Maybe you can see where this is headed.

The party got off to a bit of a rocky start. As soon as I arrived, I noticed Tyler’s ex-girlfriend was there. They’d broken up a while back and stayed friends, but you know how it goes when an old ex sees her boyfriend meeting a new woman.

That was awkward enough, but to make matters worse, another girl Tyler had dated came by uninvited. She still liked Tyler, and felt attached to him, even though Tyler knew it wasn’t going to work out…which is why he asked me to invite the hot Venezuelan over in the first place.

Of course, next thing you know the stunning Venezuelan is at the front door. Tyler could not believe his good fortune, but he wasn’t exactly doing cartwheels. See, he couldn’t really put a full-court press on the Venezuelan — not with the woman who still thought she was dating him in the same room. It’s a small apartment and there was no place to run or hide.

At this point, between his two exes (one amicable, one not so much) and Miss Venezuela, Tyler’s got more on his plate than he’d bargained for…and that’s when the fiery, headstrong Panamanian decided to show up.

She sees the Venezuelan next to Tyler and her competitive juices naturally start flowing, so she demands that Tyler make her a drink.

Tyler pulls me aside, and that’s when he says: “Oh, shit. Oh, shit. Oh, shit. What I am going to do?”

He tries to juggle the conversation between all three women when he receives a text from the ‘amicable’ ex-girlfriend who’s standing across the room. It says: “All your cows gathered in one spot tonight?”

I still don’t exactly know how Tyler got out of this jam, but I can only assume it involved my expertise as a wingman. After all, I’m still his unofficial party promoter among the beautiful Latin women community, so it couldn’t have been that bad, right?

Originally published for Five O’ Clock, a Harry’s Magazine. Words and photo by Cesar Idrobo.