My Top 5 Most Awkward Stranger Flirtations

Hi there, everyone! To start off, this past Wednesday was my 25th birthday. Therefore, we celebrate a prestigious milestone: a ¼ century of awkward. Here’s to ¾ more (because I live in the hopes that longevity and awkwardness are directly correlated).

Today on J. Awkward Prufrock, we will closely examine (and justify) my fear of strangers, particularly those of the randy male variety.

I’ve always been shy, but after a year of working in New York City, now I’m just downright vigilant. I thought I had no people skills. Who on earth taught some of these men how to woo? And then you have to wonder if it’s a trial and error sort of thing or if this stuff really has worked for them before…

Presenting my top 5 most awkward stranger flirtations. Enjoy. And remember, CONSTANT VIGILANCE!

5. Walking behind man in parking lot on my way to the bank. Man sharply turns around and points at me.

Him: You followin’ me, pretty girl?!

You have to understand that he said this so loudly and looked so angry, that despite the fact that he made it clear it was just a line, I was absolutely terrified. My eyes bugged out of my head and I think I shook a little bit. In his defense, he did follow up with, “I’m sorry. I was joking. I’m a joker, ya know? I make jokes.” Well, that made all the difference. Because when you’re sitting in a circle at a slumber party with your girlfriends, you always describe your ideal guy as “a real joker.”

4. Dozing off on the LIRR, when a conductor nudges me awake so he can punch my ticket. I open my eyes to see a (tragically) cute man staring at me from the seat in front of me.

Him: It’s too bad he woke you up. You looked so peaceful. I liked watching you.

You know what’s the worst part about train travel? There is nowhere to RUN!

3. Him: I like girls. Can I buy you a drink?

I guess he decided to add a juvenile charm to the age-old classic, “Can I buy you a drink?” Was that his tactic? Maybe? I just don’t understand why he led with “I like girls.” By posing the question, he only gave me more questions. Maybe because he was wearing a sweater vest? It is no matter, as this was long before I understood how things work, and could not comprehend why he would offer to buy me a drink when I had a full one in my hand, and I told him that, and I swear I’ve never seen anyone turn and walk away so quickly.

2. Man with teardrop tattoo grabs my shoulder and stares into my eyes intensely.

Him: I’d like to talk to you about anarchy.

Me: What?

Him: The only way we can escape is to fight it. Power. Greed. Corruption. Violence. Join my cause.

He may have not even been hitting on me. I just thought it was fuckin’ weird.

And nothing will ever top this one.

1.Walking through Times Square, make awkward eye contact with guy as he walks by, so I give him a small smile. Suddenly I hear the sound of a bag dropping and feel a pair of arms around me. He dips me. His breath is horrible.

Him (with heavy Russian accent): Hello, I find you beautiful. My name is Constantine. Meet me tonight and I will make love to you.

The thing about Constantine is that he clearly had sales training. He didn’t give me a choice about the whole making love thing. He was demanding it. I don’t think I even said a word the whole time. He was pushing his phone into my hands and before I knew it, I was punching numbers in (granted, they were not the correct numbers). I still walk through Times Square with one eye over my shoulder.


3 thoughts on “My Top 5 Most Awkward Stranger Flirtations

  1. Apparently you need to always walk with a zookeeper in the future, with a few of those cute white jackets with the arms that tie in back. While you distract them, the zookeeper can tie them up and take them to visit the other strange animals in the zoo.
    I bet you didn’t realize NYC was so fully stocked with oddballs for your entertainment.


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