Search Results: boyfriend looks young

This is assuming he’s independent, has a good paying job (not rich but above average salary), owns his own house and has an interesting life story.

I’ve tried dating again for the last three months. I’ve gotten one straight but understandable rejection from a girl in her late 20s i met at a CrossFit gym (she’s got a boyfriend). I’ve gotten two flaky rejections on dating apps (both girls in their early 30s). I did get one date with a 35 year old woman. First date started good but it turns she’s an alcoholic (has no problem drinking and driving). I wanted no part of that.

I’m 40. In excellent physical shape for my age and got all my hair. I’m 6ft tall. I’m well traveled and have an interesting past (pro mma fighter). Most women guess I’m 3 to 8 years younger than I really am.

I know dating doesn’t get any easier when you get older. But I have to stay positive (pls don’t say “all the good ones are taken”.).

But seriously I don’t remember it being this tough 10 years ago. Not even close as tough. From 28 to 32 I had a lot of pretty young girls (19 to mid 20s) interested in me. But that definitely isn’t my target age range now. Now I look for women in their late 20s to mid 30s. But why are they such a pain in the ass?

So i joined a new CrossFit gym and there is a very attractive young lady I occasionally get into small talk with. She smiled a lot today when we chatted. She knows I like her. However she has never initiated conversation with me so far. I usually say hello first. But she does engage with me when I ask her what’s she been up to.

Truth is I literally have no idea how old she is. She could be 19 or should could be 30. I’m guessing I am 10 to 12ish years older. However I’m in excellent shape and I’ve gotten dates with younger woman before. She’s also witnessing me engage in an activity where I usually out perform all the other guys around me. That doesn’t hurt. I am a former profesional mma fighter.

Anyway I am looking for an opportunity to get to know her better. However given she’s very attractive I wouldn’t be surprised she already has a boyfriend. Would it better to ask about that first or would a guy look more confident if I just straight up asked for a date? If we were the same age I would just ask her out. But being that I’m older I’m more careful about this.

If I find out she has a boyfriend then I won’t pursue it any further. I usually run into her once or twice a week. I just don’t want to make the future awkward if I straight up ask her out and she turns me down. I won’t take it personally if she’s not interested. But I go to CrossFit to relieve exercise and I just want to avoid any future awkwardness/drama