My Top 5 Most Awkward Flirting Attempts

Welcome back to Top 5 Friday on J. Awkward Prufrock!

Unfortunately, I had to miss last Friday due to my lovely cousin’s wedding. I’ll make up for it eventually.

Today, I bring you my top 5 most awkward flirting attempts. The word “attempts” is used fairly concretely here. As a lone town drunk once pointed out to me in a bar on a Monday night, as I sat there in sweatpants and a sumo-style bun, waiting for my brother to be done with work so I could drive him home: I don’t know how to flirt. Well, more kindly, he indicated that I choose not to flirt, but we all know the truth here. Flirting is chemistry, kinesiology, psychology, and art all at once. If I spent some time thinking about it, I may be able to understand one of those things on a fundamental level. However, since flirting often leaves one with mere seconds to strategize, I am generally at a loss.

Here are some very clear illustrations of such losses. Can I explain my thought process during the majority of these? No, not really. But I can say this, ladies: sometimes the nod and nervous smile just might be the best way to go.

5) Him: So, did you like the movie? Kind of sad, right?
Me: Yes. I also found it very…colloquial.
He furrows his brow, which I take as a cue for finger guns and a mouth-click.
Him: Well…see ya.

That’s what you get for using finger guns without a permit. Ah, well. Target practice makes perfect!

4) Him: You sound a little congested.
Me: Yeah, I have a cold.
He very smoothly puts up his hands in a shield-like fashion and takes a step back.
Me: That’s right. BACK AWAY!

Not only did I outright order the very cute man to back away from me, I said it with the tone and force of a chain-smoking vice principal on cocaine.

3) Guy whom I have been playfully talking to for awhile happens to be on the phone in the stairwell I happen to walk into. Accordingly, I start fantasizing about how amazingly audacious it would be if I just grabbed him and kissed him full on the mouth. It would be long and soft and sensual, and I would pull back and give him “the eyes,” and he would say, “I’m gonna have to call you back,” into his phone and hang up. Rom Com level making out ensues.
Whilst fantasizing, I am also apparently staring with my mouth partially open and an absent-minded smile on my face. He puts the phone down against his shoulder.
Him: Uh, you okay?

The unfortunate high price of awkwardness: a very active imagination and no social skills to make it happen.

2) We make eye contact through a glass door. He gives the slightest hint of a sexy smirk.
Let the nervous tap-dancing begin.

When in doubt, put on a show! Make ‘em laugh, as Donald O’Connor would say.

And, the doozie:

1) I wave goodbye to him and he blows me a kiss.
I pretend to make a small dive for the kiss and put it in my pocket. He chuckles.
(Me, internally: Oh, a chuckle! That’s right, you’re entertained! I am funny, damn. Alright, I can work with this. We have a rock-solid foundation. Now, what next? Oh, I know. I will pretend to drop the kiss. He will be so tickled and I will show off my top-notch improvisational skills! Here we go.)
I proceed to drop the kiss and run after it, ending with a slide on the floor because I am a committed actress, gosh-darn-it-anyway. I clap both my hands around the kiss and let out an exaggerated sigh of relief at finally having caught it.
I look up and see him talking to another girl.

And I couldn’t help but notice she was very much not on the floor with her hands in front of her face, but rather standing with an unfailing confidence and a hair-flip I could only dream about in my Rom Com fantasies.

Got a flirting disaster along these lines? Don’t forget to leave a comment and share!


One thought on “My Top 5 Most Awkward Flirting Attempts

  1. Number one was perfect, a true “ouch” moment. Although i do like the slide and recovery bit. Too bad that was wasted in this instance.
    I think mine was seeing a woman smiling at me, then as she walked toward me I realized she was focused on a guy behind me.


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