Dan is a 33-year-old management consultant who lives in High Park. He describes himself as “slightly above-average looking and generally laid back.” He likes to kite-surf and play golf in his off-hours. Dan’s dating life consists of a lot of one-night stands and some first dates, and he says he is looking for someone who is “very smart, funny, and adventurous—the same things everybody is looking for.” Dan met Ashley at work.
I started talking to Ashley at work a few weeks after she started. She’s in another department, so we don’t actually work together, but we saw each other around. I liked Ashley because she was really cool and into partying and having a good time, so I casually suggested we go out some time. We went out twice, and it was a good time. For our third date, I chose a new club that one of our co-workers had told me about, but I didn’t really look into it before we decided to go there.
I picked Ashley up, and we had a few drinks before going out. When we walked up to the club, we realized something was up. Neither of us suggested going somewhere else, but it definitely seemed sketchy—not like the swanky “new club” our co-worker had described. Inside, there was a dance floor, chairs, and couches, but nobody was really there. As we were standing around talking about it, a man came over and offered to give us a tour of the place. That was the first thing that confirmed our suspicions about the club being weird. He took us through one area that had lockers and towels arranged like at a gym. Then, we walked into another room that was essentially a bunch of beds on the floor. It became clear to me that this was a swingers club. I felt sick, because I was nervous about what Ashley would think of me for bringing her there.
Then, the guy walked us through a “fetish room” that had big machines and a cage. Ashley was joking with the guy giving us the tour, so I guessed she didn’t think it was an elaborate ploy of some kind. When we got back to the main area, we started talking and laughing. I was relieved, and asked her if she wanted to go, but she didn’t. We danced for a long time, and, later on, some of the other people in the room started taking their clothes off. Not long after that, we were both in towels, and Ashley started kissing me. I didn’t think I’d be into it with all of the older and not-very-attractive naked people around, but I was very horny. It escalated to the point that we were among the couples on the beds having crazy, hot sex.
Afterwards, we got out of there quickly, and agreed it was the most random thing that had ever happened to either of us. We didn’t go out another time, but we are still friends to this day.
Dan rates his date (out of 10): 10
Want to be a dating diarist? Email email@example.com.