Search Results: dating an older woman

Growing up, I was a major outcast and suffered with a lot of severe mental health issues. I had interests that were obsessive and unusual, such as an interest in fire alarms, phone systems, and intercoms. I missed a lot of school due to mental health reasons that required hospitalization and residential treatment. I hardly fit in with anyone at school, and girls especially didn't pay any attention to me. I was also (and still am) short in height at 5'6". I missed a lot of developmental milestones that I reap today.

I was never athletic in school. I was not involved in sports really. I was, however, involved in boy scouts up to age 16 and transitioned into the fire explorer programs.

Socially, I have always struggled. I was hoping adulthood would be better, but it turned out to be worse and a nightmare.

I am 27, almost 28, and I never had a real girlfriend. My absolute biggest regret that kills me to this day is not experiencing young romance. I so wish I was able to form those memories with a girl when I was young who was around my age.

It wasn't until I was around 19 when I had my first kiss with this girl I found repulsive to me. I tried dating her, but it just didn't feel right. She just was not attractive to me.

Also, there was this girl named Izzy that was around 15 when I was 18. Although we cuddled and I kissed her, she became a transgender man and resents me. There is no going back there.

When I was 20, I lost my virginity to another 16 year old girl during a weekend fling. She did not want anything to do with me romantically after that. In fact, I was convicted of stalking because of her (long story).

After that, all I have had is online things with girls where they rejected me upon meeting me in person because I was unattractive to them.

I haven't touched a girl in 7 years. Meanwhile, all my peers and former friends I have known are married and have kids.

I want a woman without a romantic past where we can be each other's first loves.

This question is specifically for YOUNG STRAIGHT MEN under 40.
I already know old men still do this commonly.

Do you pay for a woman's meal and stuff on a date? Are you the type to pay for her dinner, meals, drinks, cab fare, etc, if you're dating her?

Pretend like the date was mutually agreed upon. As if, she insisted you ask her out, and you two mutually agreed upon an inexpensive restaurant.

Honestly, I think it's pathetic and on some major cuck sh*t to still be paying for women in the 2020s UNLESS she was already a close friend and you know she's not going to be taking advantage of you. Some guys try to say "It's cause I'm a gentleman," but you can also be a gentleman without being a sucker who gets scammed by women you barely even know. I think it's antiquated and foolish nowadays, especially since many women will treat you like a business transaction and say Red Flag sh*t like "don't waste my time" as if only HER time is valuable or matters.

So I've always believed that a quality woman wouldn't treat you like a business transaction and that any hoes out there worth avoiding are the only ones who still expect men to "whine and dine" her, while she makes as much money as you do, if not more. It's total Red Flag sh*t and simp sh*t to have a grown woman expect you to pay for her in the 2020s.

What's your opinion on it?

Inspired by this question here.

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?