I'm embarrassed about who my wife dated when she was 19. She tells these stories and all I can think is why didn't you dump me?
this post was submitted on 26 May 2026
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When I was 18 and 19 I only dated middle aged women.
I can see why it's creepy the other way around.
how does that work. practically. like how were you in a situation where middle aged women wanted to date you as an 18 year old?
when i was 18 the only middle aged people i knew were parents, or teachers/professors.
the only middle aged people who approached me, were gay men.
Mostly I had a type so I was being flirty with coworkers at a couple of jobs I had. One was a bartender at a dive bar I went to that didn't care to card.
I was legal and not looking for a lot. They knew what they wanted and we just kind of clicked. Plus it was mostly going over to their place for food and sex it's not like this was some big love affair.
you were a barfly at 18? that tracks I guess.
Where I grew up most teenagers worked a lot. Hotels, restaurants, bars, etc all needed cheap labor so we had a lot of long hours at summer and weekend jobs. Most of us got included into the adult after work activities.
I grew up in a place like that but none of us were fucking or drinking with the tourists. we just drank and fucked each other like normal kids.
and nowadays, they import kids from abroad on temp work visas to do those seasonable jobs, board them 6-8 people to a single bedroom. and the tourists are not fucking those people either.
first time i met people who were dating/fucking way older people was college.
It sounds the same here. Most of the kids did the same, just drank and fucked eachother. I just was into older women and I happened to have access.
I'm 40, I couldn't fathom the effort required to date anyone under the age of 25
I refused to date people under 25 when I was 29, but got offended that a 40 year old would not date bellow 30.
I'm in my mid 40s and my hard limit is 30. I'm thinking of raising that to 35 after a few bad relationships.
As a 33 year old, I went on a date with a 22 year old and yeah I just couldn't. I felt like I was babysitting. I can date a guy 20 years older but no one younger than me
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Considering the kinds of men who tend to seek out much younger women, it's less "funny" and more "very concerning".
Hey thanks for making me feel even worse about getting cheated on and dumped by my ex when we were 19
naa. mine was at 32. my wife of 7 years, she was 41, had just died. i was alone in a house. came into money. paid off house. heard father in law tell me dont be a hermit, we love you. so i dated later that year. it was a mistake. obviously. but i wasnt alone. problem was when i “woke” i realized this person was truly using me and my vulnerability. moved on from that asap of course!
i just met someone who lost a spouse and boy... they were in a bad spot. but really really had convinced themselves they were not and that they were legit into me and should be dating and in a new relationship.
despite all their behavior being obviously that they were not into me. They were just clearly distraught/lonely and trying to fill a void, and while they were nice it was just so boring/life sucking to be around a person who was clearly just constantly living only in their memories even though they were 36.
similar boats you and I, i reckon. i mean that it’s not easy for all involved. hope things are better!
asked my wife about this, she told me to fuck off and that it she still can't talk to her mother about that.
Which is weird because I was the person she dated when she was 19
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I dated my wife when she was 19 and so was I. As I was a dick then, this all tracks.
(I'm also a dick now, but I was a dick then too #mitchHedberg)
Did you used to do drugs?
Obviously, the people who dated someone at 19 who they subsequently broke up with is more likely to regret that date. And then there are the people who are still with the person they dated at 19.
Although I guess it is true for me that my worst dating decision was somewhere around 19: I didn't make any effort to date anybody, and now that I have no dating experience at age 33, that ship has now sailed without me.
I'm not qualified to give anyone dating advice, I was single until I was 28 and then fell in love — I still have 0 dating experience.
The only way I can describe it is by brute force. I put myself in bars, hated it. Clubs, same thing. I didn't even meet my now girlfriend by anything other than random chance, and I was just about ready to give up had I not literally bumped into her.
Point being, get into the real world. Take walks, work out, live your life the way you want (just spitballing, this is not a formula). Naturally you will find others who seek to live their life the same way. Whether you make something of it or not is up to you.
Can confirm, I was awkward and embarrassing as a 19-yr old. I'm sorry to all my ex-girlfriends back then.
Granted, most of them dated me because I had a "bad boy" look and they were disappointed when they found out I was actually a quiet, introverted nerd. I was almost always the dumpee in my relationships.
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I wasn't really dating much in my late teens and early 20s but I can say for sure that the girls/women I liked around those times were absolutely awesome. They turned out great. I turned out... not so great. So... good for them.
My advice to a friend was “If he’s so mature, why aren’t all the mature women lining up to date him?”
At 19, I don’t think the advice stuck
Yeah, this argument fails to address how men get to experience relationships. One man could be your perfect partner but he simply doesn't put himself in positions to meet/date new people.
I know its easy to assume men get propositioned the same way women do but that's simply not true.
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That's basically the point.
The men are saying "She's out of my league".
The women, 10+ years later, realize that they could have done a lot better -- she was out of his league.
I think for most men it is also the lowest of our dating standards. Everyone was just so dumb.
I think you've missed that's she's referring to men in their 30s dating 19 year olds
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As a woman person I can confirm my worst choices were when I was still young and developing. I wasn’t 19, but 20.
My choices didn't get much better, but thats why I eventually stopped dating entirely. I’m a shit judge of mates, and choose the worst for me (yay trauma!!) so I just don't anymore, it’s so much easier. I’m tired of trying to grow and being brought back down by shitty men. Much rather bring myself down.
However of all the bad, that age brought me the worst. He turned out to be a convicted felon rapist (not of me. happened after he stalked me for 2 years which was itself after he moved 1300 miles to be close to me when I left him and moved home), which I discovered through court access years later. I dodged that bullet, for sure. I mean it grazed me, but didn’t hit. Sorry to the lady behind me. :(
Mine was late 20's with folks +/-2 years; I got a lot of folks wanting a father figure, or wanting a provider. The level of possessive crazy was also just off the chart.
Different strokes for different folks.
As someone who teaches 18/19 year olds (and overhears snatches of their lives), trust me, they're dumber than you remember being. It's not worth it; their priorities and yours DO NOT align.
I'm in my 40s and I've spent the past decade+ dodging ladies who want a daddy, even though they are my own age.
I never encountered any of this in my 10s/20s, people just wanted a normal partnership/friendship type of relationship. I miss it so much. I'd kill to meet a girl like my LTR in my mid/late twenties... but part of why we broke up is she basically went from being a independent and successful to demanding I pay her bills for her because she shouldn't have to pay bills because she is a girl...
It was her biggest mistake not mine!
/j
Now I feel better about the guy she left me for just as she was turning 19.
Yup, shortly before I hit 20 I got into a spectacularly bad idea of a relationship with a 37 year old woman.
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