Search Results: complicated relationships

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.

Been seeing this girl on and off (no label). Kind of a complicated situation. I'm 27, she's 20, with a really protective family and a lot of older siblings. Seems like during a 2 month period she was back in her country, we weren't together but texting, she got a "boyfriend". I didn't know until one night we were hanging out recently, her little sister said something like "insert name, misses her boyfriend". I said "what, you've got a boyfriend?" and she looked at the sister angry and said to me "no" twice. The younger one wanted to put me on her Instagram live and the girl gave her a death stare.. which now makes sense because she didn't want the boyfriend in the other country to see she was out with me at a bar at 1am. The boyfriend looks like a spotty 17 year old, so I don't know if it's like one of those weird texting kid relationship things. The other night the girl said to me "in this relationship" about me and her, and I thought she was hinting.

The next night after she denied having a boyfriend, her guy friend the same age asked her in front of me "so how's your boyfriend back home". The girl tried to divert attention but was drunk and ended up telling him "he's a good guy" this is his name etc. The same night she was walking down the street and holding my hand and flirting hard.

She knew I was mad, I went silent and cut the night short, said I was tired and took her home. Her face looked worried like I could cut her off. She text me the next day to break the ice and I was cold, but didn't say anything. I text her tonight, she said she knew I was annoyed, but I think she thinks it was because I was jealous she flirted with the friend (which I was). Quick replies between us, and then in short I said "you told me one night you didn't have a boyfriend, then the next night you were talking about a boyfriend back home to your friend". So you're either confused, don't know what you want or lied. She left it on read, but would have read it on her home screen.