What I Learned From Dating Older Gay Men

I never would have gotten to follow Laura Dern around a garden tour of Los Angeles's Venice neighborhood if I hadn't dated older men. So for that, I am thankful.

I didn't say "hi" to her, but now I think I would have. I was 21 and vaguely dating a 50-year-old guy I had met through friends. We hooked up for the first time at a huge house party I had that was filled with other early- to mid-20s people. I lived in a cement basement that, for some reason, I had painted yellow. It truly was a bad-looking room, but we were both drunk, and I was too confident to know how insecure I was. So I was really charming that night.

He was into it. I'm not sure if I was into it. But he was handsome, and I knew from friends he was successful -- at the time, anything above a yellow basement seemed really appealing. So we hooked up. It was drunk and fun. And someone walked in on us. I wondered how that must have felt to him. It seems so college to have someone walk in while you are hooking up during a party.

When I finally saw his house and his life, I could understand how getting caught sucking dick at a party with mostly Tecate being served would be appealing, or at least a change of pace. His life was set the fuck up. His ceilings must have been 30 feet high, and his parties had bartenders. When he invited me over the day of the garden tour, I think I not so subtly asked him what his parents did, because I couldn't believe someone could have this home without family money. I still don't understand how people make that kind of money -- but at 21, I really didn't.

That day was very nice. He indulged me by following Laura Dern around instead of looking at the gardens, which was definitely not the first time she had been stalked by gay men at a garden party. Afterward, we had wine with some of his straight friends. They were cozy and nice to me, but there was obviously an air of "Why did my 50-year-old friend invite a 21-year-old to my home and expect me to treat him like a person?"

By the end of the day I had done something uncharacteristic for me at that time: I asked him about his life instead of talking about mine. What were the hardest years? When did he get real? When did he make money? Twenty years after becoming successful, what did it feel like now? I gathered my information, came, and then went home to my basement. We maybe hung out romantically once more after that, but then it faded in a natural way. I still see him around sometimes, and he's lovely. This kind of thing happened a couple dozen more times in my early 20s.

When I started writing my short film Call Your Father, I wanted to not just write commentary on gay men, but I also wanted to figure out why I was consistently drawn to guys around that age. A huge theme in all my work is confidence. I think it's something gay men don't talk about enough. From the moment you realize as a gay man who you are, whether it's a challenging process or not, you know (maybe subconsciously) that a lot of the world hates you. Some want you dead.

I wasn't bullied that badly, and my parents were cool, but deep down I knew I was hated. I knew it was harder for me to get what I wanted, and a lot of that was self-inflicted. I didn't think I deserved what I knew I wanted.

What I was doing in my early 20s, by dating older men, was showing myself that maybe there was hope. That someday I could make some money and be successful and create a life for myself, just like these older men. I didn't really believe it, but being around it made me think that I'd be more likely to get it.

It didn't help, I don't think. I'm glad I did it, and I met some great men, but it didn't really help me believe in myself. It wasn't reassurance I needed. It was a genuine sense of confidence from the inside. And developing that is a slow process that I'm still working on. Most gay men never reach the end of this process, and many never start.

Both characters in Call Your Father struggle deeply with confidence -- a struggle on one side manifesting itself in real mental health issues and on the other manifesting in a lack of connection to the world and himself.

The gay confidence issue is both sad and interesting to me. I think it's what makes gay men so beautiful but also troubling. I guess if we were completely self-assured, we would just be straight men who had sex with men. A wavering confidence is part of our culture, and of course, I'd like to keep working on mine. But maybe there is a stopping point. I never want to be so confident that I am making Planet of the Apes movies. Unless they are starring Laura Dern. I think I could do well with that.

JORDAN FIRSTMAN is the director of Call Your Father, a short film about an intergenerational gay date. He is also a staff writer on TBS's Search Party. Watch the short below.