Why I Bring All My Baggage on My First Dates

The Cut
The Cut
Published in
5 min readNov 14, 2017

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By Steph Montgomery

Welcome to It’s Complicated, stories on the sometimes frustrating, sometimes confusing, always engrossing subject of modern relationships. (Want to share yours? Email pitches to itscomplicated@nymag.com.)

When I first reentered the dating pool after leaving my husband, I made a surprising discovery: Apparently, sometime during the decade-plus that I’d been married, all the single men completely forgot how to read.

At the time, I was feeling, well, like someone who hadn’t been on a first date in more than ten years. I was scared, I lacked confidence, and even though everyone I knew was telling me to “put myself out there,” I had no idea how to do that. So one night after my kids were in bed, I enlisted the help of a friend and some liquid courage, and I made myself a blatantly honest, completely straightforward online dating profile — no spin, no filters. I’m a single mom with a demanding job and not a lot of spare time to waste; I figured the more I shared about who I was, the better.

After a few super-awkward first dates, though, I learned how optimistic it had been to expect the men who contacted me to pay attention to what I’d written. Each and every time, I found myself struggling to keep my anxiety in check as I stumbled through an explanation for something I assumed…

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