Ollie
Age 37. Male. Straight.
Age 16
The Missed Camp Fling
We were supposed to sneak out on the last night of camp, except that bastard Alec never told me she knocked at the window. I fell asleep thinking of her lips and woke up regretting what I would never feel.
Age 18
The Usual Spot
She showed up with some friends to smoke, not knowing I was parked in our usual spot with someone new. The lights of the car turned on as I tried to drive away, and I’ll never forget the look she had when our eyes met.
Age 19
The Hot Goth
I found out later that she had matched with me on Plenty of Fish because she was bicurious and had never been with a man before. One night, just to see if she liked it, became one year of hooking up and a decade of friendship after.
Age 22
The Ballerina
I sat in the front row with flowers on my lap and watched her glide across the stage. She was like a beautiful fairy with grace and poise. Later that night, I saw the other side of her when she asked me to “break” her.
Age 24
The Box
As a present for my birthday, a lovely redhead joined my partner and me, and we all put on a show behind a two-way mirror at a sex club. The crowd actually applauded and cheered when we finished.
Age 27
The Ukranian
She wrote me physical letters with pretty words, to open when I felt too sad and she couldn’t text. Her feelings faded suddenly, and I think it broke both our hearts.
Age 28
Natural Selection
We met on campus before grabbing a coffee, where I told her that I was taking an evolution class, to which she replied, “You don’t really believe in that, do you?” I said I didn’t think we were compatible and walked out.
Age 33
The LARPer
On our second date, she asked if I wanted to come LARPing with her (live action role playing). Last year, I almost proposed to her dressed as a devil cowboy, but I chickened out. We were surrounded by a hundred people fighting off monsters and singing. It was epic. She broke up with me a few weeks later.
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