All Threads by Date

My Craigslist Date Last Night

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.


Thread Watcher
Click here if you are using an iPhone or iPad

DataLounge get your fix of gay gossip, news and pointless bitchery.



Talking to DataLounge servers.
Please wait a moment...