The First Date I Ever Went On With A Woman

Welcome to 29 Dates, where we explore the weird, wild and sometimes wonderful world of dating — one date at a time.

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There’s a crack in the face of my gold Casio watch. I haven’t had it fixed because the repair shop doesn’t carry that shape of glass, which is true.

I told my son it cracked when a dog pulled my watch off a table, which is also true.

A third true thing is that I love looking down at my wrist and seeing a reminder of the first time I looked down and saw my breast in another woman’s mouth.

My first date with a woman happened nine months after I left my son's father.
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My first date with a woman happened nine months after I left my son’s father. I was happy, again, and ready to date, and found myself in a completely foreign landscape from the last time around. Women! Dating apps! What marvels to behold!

I started swiping and nearly immediately connected with Vanessa*. We messaged, then texted (quite a lot for two people who swore they didn’t want pen pals), and very soon after met up. I wore a long red skirt and a tank top and an oversized denim jacket, and I felt queer and pretty and young. (The bathroom selfie I took later that night shows that exactly, plus a smile and a blush I hadn’t seen in some time.)

We went to an Irish pub in Toronto’s Gay Village, and later up the street to a place with pool tables called Pegasus. She was tall and blonde, half of her head was shaved, she had a full face of makeup and a very gay job. (She trained workplaces on LGBTQ+ accommodations and when I said that must be very fulfilling, she replied: "Not really." She only gets called in after someone’s fucked up and hassled someone in the bathroom.)

At Pegasus, we had another beer and she looked into my eyes, smiled, reached out, cupped the back of my head and pulled me towards her. We kissed and I remember thinking, This is just like the movies. We went back to her place, we kissed some more, and at one point her dog came in, which I knew because someone was licking my calf while she was kissing my face.

She later left town, and I have the watch and a good story.

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*Name has been changed

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