I usually hang out with a group of friends who are seven or eight years younger than me. All they do is take ecstasy and dance all night. I never hooked up with them, and was getting tired of that scene. I wanted to meet someone who was looking for a more meaningful relationship. One day, I found Richard on Craigslist: he was in his late 30s, professional, and said he was tired of the bullshit in the dating scene.
Richard lived in the suburbs, but came downtown a lot, so we agreed to meet the next Friday for dinner in the Village. He chose a restaurant that was adjacent to a nightclub where I had been partying every weekend. I was reluctant to go there because I was worried that some of the staff might recognize me.
On the day of the date, I was late and had to run the few blocks from my condo to the restaurant. I arrived extremely nervous and sweating, and probably looked a hot mess. I saw Richard waiting at the table. I was wearing jeans and a t-shirt, and Richard was wearing an expensive suit, and looked more mid-40s than late 30s. I shook his hand, sat down, and started chatting. I wasn’t feeling him and really just wanted the date to be over, but I was nervous. Richard talked about his world travel, his business, and all the celebs he knows. He held my hands for a while, which was embarrassing.
I thought we’d say goodbye and cut our losses. Instead, Richard kissed me passionately and asked if I would like to get a drink. Despite everything, I was getting hot, and I could tell he was well-endowed. I brought up the idea of going to a bathhouse, but Richard was horrified so I pretended to be joking. I was flattered that he was interested in me, but embarrassed about our obvious mismatch, and I didn’t want to be seen by my friends, so I suggested a nearby lounge.
I slipped myself half an X to keep my interest level up. I led Richard to the upstairs section—a closed-off, dark area with a couch. Richard told me how he was having a fundraising party at his house that weekend and that he wanted me to come as his guest. To shut him up, I started kissing and caressing him. He responded at first and then brushed me off when I got too adventurous, saying anyone could catch us. He also kept saying, “You’re bad,” and “I’ve never done this before.” I lied and told him I’d never done it either. We made out until my X wore off, and then I told him he couldn’t come over because I was tired.
The next day I emailed him, just to be nice. I lied and told him I had a great time and asked about his party. He replied a few days later saying that I wasn’t his type. I was so humiliated.
5 out of 10 for the date.