Bill is 28 years old, works at a start-up, and lives in Little Portugal. He says, “I like to play with my cat and buy large pepperoni logs (with cheddar cheese) from No Frills and eat them.” He is looking for someone who doesn’t need to party all the time and is “pretty happy reading old Fangoria magazines to me while we’re naked or in our underwear.” Bill met Martin on Facebook.
Martin messaged me after he saw some comments I had left on a mutual friend’s page. He said he thought I was cute and funny and that we should get a coffee. We met up that night. I like older men, and I found him super-attractive and attentive. The date was short, but pretty wonderful. We planned to go out again that weekend.
The second time, Martin was different. We were going to go out for dinner, but as soon as I got there, he texted me that there were no tables, so I should meet him at a nearby coffee shop to decide where to go. Martin was slumped in a chair and told me that he was hungover from the night before. I asked him if he wanted to reschedule, but he told me he never breaks commitments.
We left, and as we walked around, he mentioned that he had really bad internalized homophobia, even though he’d been out for many years. I tried to help by being cute and holding his hand on the street, but after a couple of minutes, he got uncomfortable and asked if we could just go to his house for a hot tub. Despite the red flags, I led with my cock and agreed.
His house was nice, and the home-court advantage made him seem less unhinged. He asked me about my exes, but when I asked him the same thing, he abruptly walked away. He then came back and said that the boyfriend conversation made him feel “emotionally unavailable.”
We spent 10 minutes sitting in the hot tub in awkward silence before we started fooling around. Twenty seconds later, he stopped and told me not to come in the tub. We ended up going upstairs, where we exchanged substandard blowjobs. Afterwards, he asked me if I would cuddle with him. I said I would, but soon after, he stopped and told me to get my clothes on and leave. He said that he wanted to be alone. It was a really tender moment.
As I was putting on my boots, Martin asked me whether I needed a ride home. I said no. He said, “Good,” because, again, he wanted to be alone. It was the worst date I’d ever been on. As I was leaving, he asked me out again.
Bill rates his date (out of 10): 1
Want to be a dating diarist? Email firstname.lastname@example.org.