The Top 5 Times I Ruined Everything

Two posts in one week! I’m proud of me.

Granted, it’s been a bit slow at the job I still don’t know how to do. At least, I think it’s been. There are probably 96 things I’m supposed to be doing and just don’t realize it.

It is no secret that I’m a terrible flirt. I’ve never been sure of the social nuances that constitute flirting. I mean, I’m talking to you, aren’t I? I don’t know you and yet I’m here, telling you things. Can’t you see that I’m terrified? Isn’t that enough to convey that I’m interested in further pursuing this courtship? Please ignore the fact that I just said courtship…and pursuing.

I simply cannot master appearing nonchalant, yet interested; sexy, yet sweet; mysterious, yet vulnerable. And I frankly don’t understand why we can’t just get all of our weirdness out in the open to begin with as a strategy. We’d probably save ourselves a lot of heartbreak.

Regardless, here are the top 5 times that it was over before it had even begun, the top 5 don’t-do-these-if-you-want-a-second-date tactics.

  • The Standpoint of Convenience

I mean, you can’t have him knowing you like him. That’s middle school cafeteria suicide.

Him: Well, maybe one of these days, we’ll have to hang out outside of work.
Me: Ugh, that sounds like so much trouble.
Him, trying to salvage what’s already been lost: Oh, it could be trouble *wink*.
Me: No, I mean, like, I live really far away.

  • Leave Him Wanting More

We pull into my driveway after going out for coffee. I go in to give him a hug, but he pulls my face into his face and kisses me…on my mouth, guys.

Me, pulling away, slightly frazzled:…Okay.
Him: What does that mean?
Me: Okay.

And then I got out of the car. And he never talked to me again.

  • The Candid Approach

Seeing the attractive male specimen I’ve had my eye on recently, I contort myself into a pose of available apathy. It probably looks more like menstrual cramps.

Him: Hey, uh, what are you up to?

He narrows eyes in a way that indicates he genuinely doesn’t understand what I’m up to and is legitimately concerned about my health.

Me, realizing my failure: Trying to appear aloof.

He furrows his brow as though he is still concerned but doesn’t want much more to do with the matter and walks off to find a better life.

  • Show Him Your Dirty Talk

A cute man in the bar does not immediately see I am behind him and accidentally slams door in my face. Realizing his error, he opens the door again.

Him: Ack, I’m sorry.
Me, in an attempt at a joking tone: Yeah, well, fuck you.

He is clearly crestfallen and confused by my remark.

Me: I’m sorry, that was really unnecessary.

He is still staring and I am not sure what he wants from me.

Me, taking my best guess: I was just…you know…you…and your face…and aaaahhh.

I run past him through the door, flailing wildly into the bar fray, desperately in need of a whiskey sour and new manners.

  • Play Charades

We introduce ourselves, and I just giggle because I am not sure what to say next.

Him: Oh, I get it, you’re the awkward girl.
Me: Yeah, I guess so.
Him: Yeahhhhhhhhh…

We stand in silence for what feels like 87 years.

Him: I’m gonna go.

That last one was actually a bit of turning point for me. You know how you never realize some things about yourself until someone points them out to you? It’s not as though I didn’t know I was shy or didn’t know I wasn’t great at making friends. But I finally had a name for what I was like in social situations. I was Jillian, the awkward girl. I was the girl who took off her shoes but left on her coat. And this was my story.


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