Search Results: dating an older guy

I remember getting in my first big age gap relationship at 28. I was dating a 20 year old. It was a weird combination of excitement, fear of judgment, concern about maturity and yet youthful fun and vigor. I was also the oldest guy she ever dated too. That one didn’t work out. She was very immature and a freeloader. I also sometimes acted purposely immature out of fear of looking too boring/old. There is a playful way to do that but you need to switch it off fast in when you are expected to be an adult. Not always easy to switch.

I’ve been in 3 other age gap relationships. Biggest gap was 34 and 21. That was doomed to fail from the start but we had a ton of fun while it lasted. She ghosted me after 9 months and I was surprised it lasted that long. The ghosting still hurt and was complete bullshit. But I knew that risk came with the territory.

I’m not opposed to dating women my age. As long their relatively attractive and have a positive attitude I’ll give it a shot. But here are the challenges:

- They are far fewer single women my age.
- They are usually divorced and/or have kids. Not a dealbreaker but it definitely complicates things.
- I also noticed single women my age forget how to be fun. I briefly dated a woman a year older than me and I was shocked/pissed off that she thinks it still okay to shit test men on sexual stuff. She lead me on and changed her mind at the last second. A grown ass woman should know better than that.
- If I want to get serious with one than having kids could be a bigger challenge.
- Some older single women are just mentally unstable. I know that same standard could be applied to me. But as a man nobody is taking a knee to propose to me in marriage. Being single at my age has much different ramifications (and bad stereotypes) as a man vs. a woman.