How to Flirt with a Total Stranger without being an Asshole

When I think of men flirting with some on the street, I think of catcalling and stalking and rude gestures. I think of feeling uncomfortable at best and unsafe at worst. So when in public, I tend to avoid meeting men’s gazes because I want to minimize those possibilities as much as possible. Imagine my surprise, therefore, when an encounter in Italy, country of notorious womanizers, taught me how to enjoy being flirted with!

In Venice, I stood in a shop waiting for my mother to buy us water taxi tickets. A man walked in a stood next to me, also waiting in line. He was well-dressed, with a button down shirt, khakis, and grown-man shoes. He caught me looking, and as always, I cut my eyes away in order to pretend nothing had happened. But when I glanced back, he was still looking at me. He held eye contact and smiled. I smiled back. He turned to the counter. A few minutes later, he paid for his whatever, and as he walked past me, he made meaningful eye contact again, smiled, and said, “Ciao.” I whispered “bye” after him and was left with a really pleasant heart palpitation. 

That’s how flirting should be!! I was left feeling admired AND empowered, and I thought long and hard about what set this apart from other unwanted male attention. Here are my thoughts. 

  1. He looked like he cared about his appearance. There is some kind of weird power imbalance when schlubby men catcall women in dresses. I’m not saying you’ve got to be hot to flirt with someone, but the attention feels a lot more flattering coming from someone who looks like they understand personal grooming.
  2. He made eye contact. There was no gross lingering looks up my body. He looked at my face. 
  3. He smiled. Smiling is so hot. Yelling or sticking your tongue out is not.
  4. He didn’t expect anything. He left the shop, and we got to have a nice “ooo opposite sex attraction feels!!” moment without making a big thing of it. 

And…that’s it. It’s REALLY that simple. I dream of a world where male/female interactions are characterized by pleasant flirtations more than “oh God is he a rapist?” fears. And I think if everyone follows these four steps, we will be a little closer to getting there!

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