First Dates

The Set Up

Blind dates have a bad reputation and I’ve always been curious as to why. One friend knows another friend and, for some reason, thinks the two of you will hit it off. Can’t be that bad, right? Well, I don’t know about blind dates but I let a friend try to set me up this weekend and, I can’t even lie, I was blindsided by how bizarre it was.

Alright, the background:

My friend comes over for a drink Friday night. We’re sitting around chatting and he tells me about his oh-so-charming, really sweet, super smart friend. He thinks we would really hit it off. Will I let him set us up? Ok, sure, whatever. I like charming, sweet, smart guys as much as the next girl. Send him my way. Toss him my number. Throw me a bone. Whatever. But that’s not how it turns out.

Here’s how it turns out:

It’s the Saturday of the weekend before Halloween. I am dressed as a bridezilla,  decked out in a full on bridal gown, bustle and all. I have plans to powwow with some girlfriends at a house party but will inevitably end up in a bar. My friend texts me – I’m with said charming/sweet/smart guy, what are your plans for the night? he asks. I give him details but continue on with my life, fiestaing at will. We hop from bar to bar and find ourselves in the classiest of Chicago’s neighborhoods, Wrigleyville at it’s finest. We hang around a bit and finally, I’m lured down the street to meet up with my friend and this potential charmer. First, I should mention that neither of these men were wearing costumes. So I was being introduced to a supposedly potentially date-able person in Wrigleyville, at a bar, at 2am, he’s in normal close, I am in a wedding dress.  Did I mention that by this time I’m solidly sober? That’s not even the worst bit. The worst bit goes like this: friend brings over the potentially date-able and introduces us then ever so gracefully steps outside to let us chat. How’s your day been? I say. Tiring he says. How do you know (mutual friend)? he asks. Oh, from high school! You two went to school together, right? I reply. Yeah, hey, listen I’m sorry but I have to go. Could we maybe continue this conversation at another time? says he. And off he goes. Leaving me somewhat dumbfounded, standing soberly in a wedding dress. Stood up at the bar after 90 whole seconds of conversation. Now I know some guys have commitment issues, but come on dude, the dress is just a Halloween costume! Essentially, I was like…:


Ever so charmingly, the mutual friend assures me that I am neither repulsive nor smelly and that the guy had been trying to bail pretty much all night, and that I really shouldn’t over think things. It still stung.

So now I’m rethinking my whole stance on set ups and blind dates. If it can be that awful in 90 seconds, I’m literally cringing at how painful an entire dinner could be.


Ouch. Wine would certainly be needed.

Thoughts? Anybody ever been set up successfully? I’m suddenly feeling very skeptical…



One thought on “The Set Up

  1. Pingback: The Set Up (Part II) | Diary of a Serial Dater

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