Confession #12 – Boston, MA

Accidental Date (1)
Illustration by Elizabeth Simins


Yesterday I went on an accidental date.


When “John,” an old friend-with-benefits, called me up out of the blue, I was confused but pleased. Though our history suggested that his interest was less than platonic, I knew he’d had a serious girlfriend for the last two years, so I wasn’t fussed about having to explain that I have a boyfriend and am no longer available for/interested in casual sex.

In college, John and I kept one another on the back burner, comfortable insurance for whenever our more serious relationships fizzled. We enjoyed each other’s company–in bed and out of it–but there was no real desire. Just fondness, and a very mild attraction. He was a super-Muslim when we met, and I an ex-super-Jew. His perspective on religion was fascinating, and we had many rich discussions, but I was too conflicted about my OWN religion to stomach dating someone with a strong background in another religion. So our relationship was strictly friends-with-benefits. We talked about our respective (lack of) faiths, but didn’t have to deal with the emotional fallout from each other’s weekly hashkafic crises.

I was confused when he suggested that we meet for dinner; our MO had always been…casual. Dinner suggested a date. Plus, I like spending dinner with my boyfriend, who works all day, and assumed that John would feel the same about his serious girlfriend. After much back-and-forthing,  I finagled a 2pm coffee date. Nothing sexy about coffee breath in broad daylight!

Given our history, I guess I wasn’t overly surprised when I found out from a mutual friend that John was newly single, but I definitely wasn’t pleased. Don’t be egotistical, I chided myself mentally. Maybe he just wants to catch up!

This delusion persisted until we met up, and it became clear and obvious that this meeting was supposed to be a prelude to rebound sex. Nothing could have been less appealing to me; I had been slightly worried that seeing him might remind me of the joys of singlehood, and make me wistful for my carefree college days, but all I wanted was for my boyfriend to be sitting in front of me. Spending time with another guy was boring in comparison.

When I mentioned my boyfriend, John’s face actually fell, and his expressive green eyes dimmed. Sounds like an exaggeration, but the boy has always worn his heart on his sleeve. I’m not kidding myself that he was torn up over me. He was just lonely–post-breakup, miss-my-boo, newly-celibate, busy-grad-student lonely.

I left the “date” as early as possible. After a long hug, during which I pounded his back as bro-ily as I could, I said “dude, this was sweet! Let’s do it again sometime.”

“Definitely,” he agreed, lackluster.

I know he will never call.

– Female, 25, Boston (MA)

Confessions are anonymous collections of your deepest, darkest secrets. Share your confession today.
  • Mismatched expectations. They almost always lead to awkward situations…

    I enjoyed this line: “After a long hug, during which I pounded his back as bro-ily as I could, I said…” Bro-ily? Heh. Poor guy. Poor you. Thanks for sharing.

  • Anonymous Internet Commenter

    Good god this sounds awkward

  • I have been there. Oh, the mountains of awkward.