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DTA

DTA

Desperado
May 3, 2025
100
So, I'm what I refer to as an old man now. Middle-aged, technically, but not a young buck anymore. I spent my late twenties and most of my thirties in prison and since getting out I've been shocked at attention I'm getting from women.

I'm going to lay out a bit of my past to illustrate where I'm coming from, but I'm really curious if any other middle-aged men have similar experiences.

When I was young I was cheated on by multiple girlfriends. In youthful naivete I reasoned that all women were just going to use me so I decided to use them first. I quit dating and started just chasing tail. I would hook up with as many women as possible. At my best (or worst, depending on how one looks at it) I had a different girl for every night of the week.

Eventually I fell in love with a long-time platonic female friend and we eventually got engaged. I swore off all other women and was loyal to her alone. And she cheated on me on Christmas Eve. With my sister.

Since then I've been voluntarily and comfortably single. The whole womanizing thing left me somewhat hollow and I'm unable to trust a partner. I was even able to ward off another young man from walking my path. What's more, the thought of being physically intimate with anyone is revolting to me now. I never had any difficulty in prison for lack of sex like so many other men did because of that fact. And now that I'm out I'm just focused on taking care of an elderly woman who needs my help. I don't want to have a partner.

But what I find bizarre now is the attention I'm receiving from women. I used to have to work to get female attention. I've always looked young and due to my Native blood I can't grow a beard, even now. I was reasonably good-looking, I think. Average height. Slim. Relatively fit. Fashionable. But females weren't exactly throwing themselves at me. Now I'm middle-aged. I've filled out a bit and have a bit of a beer belly. A dad bod, I guess. I look young for my age but I'm not a svelte young sex machine anymore. I'm certainly not wealthy.

But I come back into the world and I suddenly find much younger women throwing themselves at me! I used to love playfully flirting but I don't even do that anymore. I'm not interested!

Yesterday at the grocery store I was buying food for the old lady I help. There were three teenaged girls at the checkout: a clerk, a bag girl, and another employee who was just hanging out with them. They made a big fuss about the Asian food I was buying and started heavily flirting with me but I didn't respond to it. There was also a young woman I met recently in a different town who was hitting on me. I told her, "You know I'm old enough to be your father, right?" She sort of backed off but didn't seem to lose much interest. Those are just two cases that come to mind!

It reminded me of my childhood with my much older father. I was 10 at the time and he was 73. We were similarly at a checkout with a pretty cashier who couldn't have been over 18 or 19. She asked if I was shopping with my grandpa and I told her, no, that's my dad. She said, "Oh?" and then started hitting on him hardcore. He just laughed it off but I was shocked that she'd be after an old man like that. "Go Dad!" I thought.

And recently I was seeing videos on YouTube of young women going absolutely nuts over Leon Kennedy in the new Resident Evil game. Leon, who is supposed to be in his 50's.

So my question is, is that typical of women to chase older men like that? This is all new to me. In highschool girls my age were after college boys, but I never saw them chasing middle-aged men. Are there any other old men like me who've experienced this, or have I just had weird luck? Is it the fact that I'm NOT chasing these young women that draws them in? Or heck, maybe there's women here who could shed some insight into it!

I'm really curious about this. The psychology of it. I'd be grateful to anyone who could share insight.
 
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pax420

pax420

Happy last birthday to me!!!
Jan 19, 2026
132
You just got weird luck. Lol I was with the same woman for 23 years until she died. During that time I was hit on more times than the rest of my life. Mostly by her friends I guess they seen how I treated her and liked that. Now I'm old about to turn 57 and women run from me lol. I don't want another one at this point I'm my life I was just glad to have had her for our time together. I'll never find anybody who could compare to her so I don't look. So I guess what I'm saying is consider yourself lucky. Glad you got out of prison. I didn't do as much time as you but anytime in the system sucks.
 
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DTA

DTA

Desperado
May 3, 2025
100
Thanks for the insight.
I guess maybe "luck" was the wrong word to use since, like you, I'm not interested in getting with any of them.
That's interesting about women chasing you when you were married. I wonder if it's a similar thing. Like, one of those things where people want what they can't have.
 
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violetforever

violetforever

Warlock
Dec 24, 2025
769
Eventually I fell in love with a long-time platonic female friend and we eventually got engaged. I swore off all other women and was loyal to her alone. And she cheated on me on Christmas Eve. With my sister.
a literal villain backstory.
Since then I've been voluntarily and comfortably single. The whole womanizing thing left me somewhat hollow and I'm unable to trust a partner. I was even able to ward off another young man from walking my path. What's more, the thought of being physically intimate with anyone is revolting to me now. I never had any difficulty in prison for lack of sex like so many other men did because of that fact. And now that I'm out I'm just focused on taking care of an elderly woman who needs my help. I don't want to have a partner.
im not even a man or nearly as old as you but same. i prefer to be single, ill never trust anyone and i dont want to have sex. it was a womanizing man who led me here lol.
I used to love playfully flirting but I don't even do that anymore. I'm not interested!
yeah ur better than me. thats my favorite thing. i wish i could lose interest in it because it gets me into trouble.
It reminded me of my childhood with my much older father. I was 10 at the time and he was 73. We were similarly at a checkout with a pretty cashier who couldn't have been over 18 or 19. She asked if I was shopping with my grandpa and I told her, no, that's my dad. She said, "Oh?" and then started hitting on him hardcore. He just laughed it off but I was shocked that she'd be after an old man like that. "Go Dad!" I thought.
is ur dad clint eastwood?
So my question is, is that typical of women to chase older men like that? This is all new to me. In highschool girls my age were after college boys, but I never saw them chasing middle-aged men. Are there any other old men like me who've experienced this, or have I just had weird luck? Is it the fact that I'm NOT chasing these young women that draws them in? Or heck, maybe there's women here who could shed some insight into it!
u literally said u got with a new woman every night when u were younger. it doesnt sound like u ever struggled to get womens attention. i think ur actually just attractive or have some attractive quality about u. maybe thank lana del rey too.
 
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DTA

DTA

Desperado
May 3, 2025
100
a literal villain backstory.

im not even a man or nearly as old as you but same. i prefer to be single, ill never trust anyone and i dont want to have sex. it was a womanizing man who led me here lol.

yeah ur better than me. thats my favorite thing. i wish i could lose interest in it because it gets me into trouble.

is ur dad clint eastwood?

u literally said u got with a new woman every night when u were younger. it doesnt sound like u ever struggled to get womens attention. i think ur actually just attractive or have some attractive quality about u. maybe thank lana del rey too.
Lol
Dad would have preferred John Wayne. He was a Marine and a former boxer, among other things. Mom loved that, as she said, "He was all man." But he'd still cuddle a little dog or cat when he thought no one was looking.

For the pickup thing, I really had to work at it. I'd say I'm a 6. Maybe 7. But I just learned what to say and how to act. And for every "success" I got shot down a few times. But that's also what I'm ashamed of. It was all manipulation.

I guess that's why I'm so confused now. I used to have to put in a lot of work to attract women, but now I'm not doing anything and getting way more attention.

Yesterday I found a YouTube video from a woman's perspective about just this topic. She says that women can tell when a man isn't trying to attract women or hit on them so the women feel safe and can relax. She said they aren't necessarily flirting but just relaxing enough to be truly friendly. As a woman do you think there's anything to that theory?
 
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