Search Results: dating older men

I went through this about 10 years ago. My then 25 year old girlfriend made more than me when I was 32. But at the time I was pursuing a dream (I was a professional athlete) and I my time was consumed with training. I was no dead beat but I just had a different focus at the time.

I was doing freelance work just to pay the bills and I was struggling. She even offered me money at one time (which extremely kind of her) but it I turned it down out of pride and went further in debt.

Anyway the insecurity was on my side when it can to this (also contributed to our break up). She didn’t care but I did. It had a lot to with being raised to “be a man” when it came to being a breadwinner.

Nowadays I make a lot more money given I’m retired from my sport and have full focus on my career. But I am also a lot more “boring” now since I’m no longer the free wheeling adventurer I once was.

But money is a touchy issue. Form a evolutionary perspective I really do believe most women still subconsciously expect a man to provide for them even it’s unnecessary or impractical. They might get into short term flings with guys who offer other benefits (looks, excitement, adventurer, personality, etc) but when it comes to long term commitments they have a much higher bar on this

I also believe when a woman makes more money then her boyfriend/husband she’s more prone to cheating. Especially if she is comparable to him when it comes to looks (maybe she will stay loyal if she’s physically unattractive compared to him)

In fact I believe it’s unfairly more socially “acceptable” for a woman to do this given the guy is considered a “chump” if he is financial dependent on her. More more acceptable then vice versa.

I have a divorced uncle who worked a low paying his entire life and was supported by his (comparably) rich wife. She was no multi millionaire but she earned a lot more than him.

She ended up cheating on him the entire marriage. He tolerated it because they had kids and he needed support.

Lost hair to a telogen alopecia at 18. Shave what’s left. Still have eyebrows and most body hair. I’m a decent looking guy, even told I’m handsome by many. But I’m 28 now and I’ve just had no luck dating. Never even been kissed or on a date. I’m very social, involved in many groups and activities, went through 4 years of college and always had big social circles. So so many times women have shared how they can’t believe I’m single etc but yet, sometimes even those same women, turn me down. There’s been a small few who were into me but honestly I just wasn’t attracted to them. That physical attraction has to be there as well as the emotional one. I got one life and I am not settling on what I want just due to a genetic condition. But I don’t blame the women who aren’t interested either, looks do matter, just sad to think hair really is such a big determining factor for men’s looks and there’s nothing I can do but wear a wig (which I actually started doing-a full custom one, it’s 2024 and makes me happy).

But yeah, I’ve probably asked out 40 odd women in the decade I’ve shaved my head, all no’s. About 12 made it clear it was the baldness. (I always journal so I have reread this many times and remember the numbers, probably not healthy) and I’m sure others were the same. Just sad, really wanted to be married to a young woman I found beautiful and who I loved dearly. Didn’t care about much else. Not interested in waiting until I’m older, nor in dating women older than me. I’m 27.

Honestly friends I think I may clock out here soon. Love each other out there and please be kind. We all need to learn to take rejection yes but please be kind giving it. This world is mean enough.