Age-gap relationships have long been a subject of debate due to what many view as unfair power dynamics, particularly if the relationship is between a younger woman and an older man. It goes without saying that not all age-gap relationships are inherently unequal; however, they do seem to have a much higher incidence of these dynamics...
That's why when Redditor u/Confident_Gazelle438 asked, "What's the biggest age gap you had in a relationship, and do you regret it?" People of all ages shared their experiences with age-gap relationships and the reasons why they'll never, ever do it again. Without further ado, here are 17 of their most jaw-dropping responses:
1. "He was 59, and this took place when I was 28. I liked dating older men in the past and decided to give it another go, but I quickly remembered why I stopped dating much older men. I regretted it so much that I will no longer date anyone who is 10+ years older than me. Age, turns out, does not always make you a mature person."
2. "When I was 23, I was with someone who was 40. I thought it would be harmless fun at first, but she was emotionally immature, manipulative/coercive, and had some other issues going on. She didn't listen to or respect me when I would tell her 'no.'"
"I broke it off with her when I started dating someone else, yet I would wake up in the morning to 40 unread texts from her, all paragraphs long. She would show up at places I frequented, trying to run into me.
Eventually, I had to block her number and change my entire schedule to avoid seeing her."
3. "He was 12 years older than me, and yes, I regretted it. He was a 30-something man-child who didn’t know how to take care of himself and relied on his 19-year-old girlfriend to clean up after him. He borrowed money from me when he was broke and never repaid me when I helped him land a job at a super successful tech company. He later cheated on me with his best friend’s girlfriend."
4. "I’m going to answer on behalf of my parents: They had a 12.5-year age gap (they married when my mom was 23 and my dad was 35, and it was his second marriage). They stayed married until my dad passed at 79, but it was a tough marriage that seemed to have many highs and lows. My dad was 45 when I was born, so he was an older dad but acted much younger, so it didn’t seem to affect them at first. His first family was occasionally a bone of contention between my parents, but the challenges of their age gap really started to show when he was about 60, and Mom was still in her forties. I think this is the point where she was no longer propelling him forward, and he was slowing her down – or at least trying to."
5. "I was 19, and he was 29. It was my first adult relationship, and I was hesitant because I told myself I was okay if a guy was up to five years older. He told me he was 26, which was stretching it already, but two years later, his friend accidentally told me that he was even older than that – actually TEN years older. The lie undermined our whole relationship."
"At 19, I would never have gone out with him if I had known he was a decade older. But he took away that right and even said that is precisely why he lied: so I would date him.
We broke up shortly after that because I felt I had been tricked – no man should date someone with the word 'teen' in their age."
6. "She was 19, and I was seven years older. It cemented my rule to never date anyone that much younger. She was still going through that late teens/early twenties 'I hate my parents' stage, and she was raging against the need to have a job, pay bills, etc."
"Truthfully, I only dated her because we were out in the sticks and there just weren't very many 'subculture' people around out there.
She also wasn't very good in bed. I don't know why our culture promotes this sexual fascination with women in that age range, but women in their thirties are much better in the sack."
7. "It was a 12-year gap. I was twenty-five, and carried a lot of guilt for years because 'I should have known better.' It became intimate partner violence, and the age gap wasn’t the first thing to blame, but it was part of a greater power imbalance. I heard both sides of the 'You’re so put together for your age, I don’t even think about it' and 'I’ve got over a decade more experience, so listen to me.' It would have been bad even without the age gap, but it was used against me when convenient."
8. "I think it has to do more with the time of life than years. It wasn't the most egregious age gap, but I was 20, and he was 30, and he definitely took advantage of the fact that it was my first serious relationship and treated me a way no woman his own age would have tolerated."
"As someone now in my thirties, it's wild to think about how I would not ever date a college student like that."
9. "It was a 16-year gap. I was 18, and it was my first age-gap relationship. It didn’t last long, but later I married twice, and each of my ex-husbands was 15 years older than me – none of those relationships were healthy."
"I completely forfeited who I was to make men happy who didn’t like me as a person (both of them eventually flat-out told me this) and didn’t want me to develop as an individual.
I am in the lifelong process of de-indoctrination from codependence."
10. "I was 17 when we got together; he was 27. I never got to go out, have fun, or drink with friends. He alienated me from all my friends, so it was very lonely. I was dependent on him and my mum. I felt extremely controlled, so I finally left after 10 years. I massively regret it."
11. "He is 13 years older, and now that he is pushing 70, it isn't that great. I'm more active, and he can't do what I do. He doesn't stop me from doing stuff, but he has to wait on me. I don't have a dance partner at events, and I get a bit sad and jealous of my friends who do (this is just one example)."
"I most likely won't have a partner to grow old with, and I didn't think of that in my mid-twenties."
12. "He was 12 years older. I was in my twenties, and he was in his thirties. I was his first serious relationship, and I ended up spending years trying to teach him basic communication skills, empathy, how to take accountability and apologize, and generally how to be a good partner. I also had to handle all the planning (dates, travel, etc.)."
"I learned the hard way that you can lead a horse to water, but you can't make it drink. I felt like his manager/mother, all while I was trying to grow up myself.
I feel like I wasted what were supposed to be some of my best years on him – so yes, I absolutely regret it."
13. "I was 21, and he was 34. I don't necessarily regret it, but in hindsight, I wish we never got together. I think the only good that came out of our relationship was the experience and our daughter. We were together for almost five years; we’ve been 'separated' for a few months now, and I’ve been happier and less stressed than I have been in years. Ultimately, I think nobody should 'regret' their relationships; rather, take that experience and apply it next time. It molds you into a better person, in my opinion."
14. "It was an eight-year gap, and I have lots of regrets. We had a lot of problems, and one of them was that she cut short a phase of life that she shouldn't have – namely, that phase of your twenties where you are most independent and free in your life.
"She definitely romanticized the idea of it, but she felt trapped in part because she didn't know that it's such a mixed bag. It's freeing, and you can live on your own terms, but it's economically difficult and lonely."
15. "It was the worst mistake I've ever made. I was 22, and he was 41. He was toxic, controlling, and clearly trying to groom me into his idea of a 'perfect girlfriend,' and young, naive me thought that was 'love.' He seemed fine with my likes and dislikes at first, but gradually started to police what I wore, what I listened to, tried to alienate me from family and friends, and made fun of my accent. He made more money, so he controlled me financially as well."
16. "I dated three men who were ALL 12/13 years older than me when I was in my mid-twenties (these relationships were a couple of years apart). I think most people assume it’s obvious that older men go for younger women for looks; I actually think it’s because emotionally vulnerable or immature men feel safer and less judged by younger women."
"Now that I’m in my late thirties, I only regret feeling like I was a fool or a child after the relationships ended when it really came down to being in different life stages."
17. "I dated a guy who was 22 years older than me for a little bit. I was 22, and he was getting ready to turn 44. He was lovely, but he didn’t jive with my working two jobs and still partying/going out with friends regularly. He was angry too, that when we first started dating (before we had an exclusivity talk), I slept with someone else, and that I had a friends-with-benefits situation before we even started seeing each other. He had just gotten divorced from his wife of 20 years, and I think it was my lifestyle that threw him for a loop after a life of monogamy."
Did any of these stories surprise you? Have you ever been in an age-gap relationship? How was your experience with it? Feel free to tell us in the comments or answer anonymously using the form below!
Note: Some responses have been edited for length and/or clarity.


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