#26 Ask Out a Total Stranger

This list item has the distinction of being the single most frustrating and anxiety inducing item on this list. Over the last ten months I never really found myself in a good position to ask a dude out. I was either at work, at the supermarket in my gym clothes all sweaty, or at the gym in my gym clothes all sweaty. I thought about asking a guy out at one of the many wrestling shows I attended over the last year, but something about asking out a grown ass man wearing a Rey Mysterio mask was off putting to me.

Now, I’ve asked out guys before, so that wasn’t the thought behind doing this task. The thing is, I have never just looked at a guy and been able to say “Oh, what a stallion!” without getting to know him first. I assume all good looking guys are assholes and I haven’t talked to enough of them to be steered away from that concept entirely. My crushes include a British wrestler and Rick Moranis in “Little Shop of Horrors.” I wanted to able to look at a guy, experience that sort of “love at first sight moment,” ask him out, find out he’s gay/married/lying about being gay or married, and move on.

And then one day at the bar after dodgeball I realized that I had a type. Chubby, bearded gingers with tattoo sleeves. Glasses are a nice added bonus. I tried talking to CBG each time he brought up his trivia answer, but I could only ask stupid tattoo related questions and it was obvious I was trying too hard. Plus, do you know when the worst time to stop someone and talk to them is? When they’re trying to win a trivia game.

Yesterday at Suffolk Downs I saw one. And if you read my previous post you know that he must’ve stuck out like a sore thumb. To be honest, I’m not entirely sure that this guy even exists. I could have just imagined him amongst the walking dead of Suffolk Downs because my eyes could not handle that much sadness. By the time my instinct to ask him out kicked in, it was too late. He vanished into the night. My CBG Bigfoot. He must be found.

And so I have turned to the search party known as “craigslist missed connections” to help me locate him, because, as dumb as this sounds, for the first time I cannot get the physical image of a person I have seen in real life out of my head. I totally want the opportunity to ask this guy out, so I have to make it. And receiving an anonymous email is the best way to go.

Today is my birthday. This was the last item I needed to do. And it totally counts as a ballsy move because I had to actually admit that I posted a craigslist missed connection.

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3 responses

  1. I read an article about people who met on a plane and then later found each other over Craigslist Missed Connections and got married. CBG could be the one! Of course you have to go for it.

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