Winning at Dating

Mary, Mary, Quite Contrary
4 min readFeb 18, 2023

and dying of fuck boy abandonment

oil painting generated by the author with Dall E

My lack of experience with dating and general anxiety about the world has turned it into an activity that I hate with a passion. But I think I’ve really figured out how to do it better.

I’ve really found my sweet spot with it. I am approaching it with a sense of openness and whimsy. I am genuinely dating without expectations and worry for the first time in my life. I’ve even managed to find some mindfulness in using the goddam apps. I’ve only got one installed, and I only look at it once, maybe twice a day. And I swipe through a few bachelors in my area and see if anyone of note has messaged me.

And this works well until I match with a guy that I am really into. Then I turn into an obsessed idiot that can’t put down my phone. I spend hours trying to construct a reason to message my obsession of the week.

My current obsession is Jay. He’s tall, hot, broad-shouldered, funny as fuck, and he turns me into a blushing idiot. Our first date was at Starbucks, and was uneventful until he started to flirt. It was such a hard right turn in the conversation that I almost fell off my chair in disorientation.

“I have the feeling you’d be fun to tease?”

I bit my lip and my Starbucks straw and said, “what makes you say that?”

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Mary, Mary, Quite Contrary

Mary is a writer of memories about bad experiences in Polyamory, surviving divorce and experiments with sex and dating, over 40.