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“Biggest Cheater Ever”: 21 Honest Age Gap Relationship Stories Shared By People Online
Article created by: Ilona Baliūnaitė
Age gaps—they’re a pretty controversial topic when it comes to relationships. Some say it’s fine as long as it’s between two consenting adults, while others think it’s always a bad idea.
Either way, these Redditors decided to open up about their experiences dating someone much younger or older. Read their stories below to see who found lasting love and who walked away with heartbreak, and let us know what you think in the comments!
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#2
I was 24, and she was 36. She was a family friend.
I just messaged her on Facebook spontaneously, and she asked what was for breakfast. I told her chorizo and eggs, and she asked if she could join. I obliged.
The relationship lasted 10 years
#3
My boyfriend is 12 years older than me and only six years younger than my mom, but she had me young at 18. I’m also only 10 years older than his son.
When you do the math, it’s weird to think about, but we fit really well together.
None of our friends or families blinked when meeting either of us because they didn’t realize our age difference, and by then, they didn’t care.
We’re expecting our first child in March, and our families are more excited than we are, lol (laughing out loud).
#4
I'm 30, and he is 48. We have been together for two years. I met him on Grindr as a casual hook-up, and we fell in love with each other.
I left my job and moved with him 400km away from home. I have never been happier.
#5
When I was a teenager, I got involved with a hobby that peaked in popularity around the time I was born. In college (this is around 30 years ago), I started attending conventions and meeting other devotees in person. Most of them were 15-20 years older than me. I also started being part of an Internet community. Almost all of my friends that I made as an adult were from this same hobby. Some people treated me as a peer, some as a little sister hanging around. A bunch of us all traveled to this one event - my husband was a friend of the people I was traveling with. It's like I didn't meet a stranger, but a vetted respected member of our community. When we met, I was 21 and he was 40. We got together a year later. Now we are 49 and 68 - we just celebrated our 22nd anniversary.
The first other devotee I met was when I was 16 and this guy was 29. He lent me books and other media, we hung out a lot (in public), and he gave me rides a couple of times. Looking back, it was strictly above board, but I was lucky. We're still in touch.
#6
When I was 43(m) and newly out of a long term relationship I had a couple of short relationships, a few months apart - slightly more than flings - with a 27yo and a 29yo. The 27yo was long distance and we met because we had mutual friends on Facebook and she specifically messaged me to flirt. It ended because it was long distance, really. No harm no foul; we still are slightly in touch. The 29yo I met on Tinder and was a little fast to push for the bf/gf label. I broke it off because, frankly, I eventually got the impression that she was not single and I was her side piece.
Both admitted to having a thing for older dudes, and neither lasted long enough for any age gap stuff to get weird.
About six months later I met a gal 5 years older than me. We’ve been together 6 years and married for 1. :D.
#7
I met a woman on Tinder who is ten years older than me. I’m 34 and she is 44.
It felt weird at first, but I get along with her better than any of my previous partners. Age ain’t nothing but a number is a real thing, to be honest.
The big thing is she has kids, and I don’t, but right now, we’re just keeping things between us to keep things simple.
If we end up getting more serious and stay together long term, I think she’ll meet my folks, and I’ll meet her kids. I don’t know what the future holds, but she is an awesome person, so I don’t think I’d be opposed to that happening. Being a step parent seems pretty intimidating, though.
#8
I went to a bar with my mom when I was 23. The door guy asked me for my number. He was good looking and in great shape but obviously much older than me. He was 37. I gave it a shot. We dated 8 months. He seemed great, had a day job working with disabled people, was very stable, good with money, even tempered, and health conscious.
He was the biggest cheater ever.
Edit: thanks for all the karma, Gary.
#9
We hit it off through a book club. Age didn’t matter because we were both passionate about the same stories and ideas.
#10
Met online in an MMO.
Our play styles complemented each other, so we started grouping together every time we were both online.
The more we grouped, the more we talked.
Real life subjects started coming up more and more.
The more we learned about each other, the more attracted we became to each other.
We became damned close.
It took 2 years to realize there was a 20 year ago difference between us.
Decided to meet up in real life.
Once we were together age didn't matter at all.
That relationship lasted 8 years, and only ended because both of us were too stubborn to move away from our respective families.
This was all before voice chat was a thing in MMOs, or online at all.
#11
Chatted her up at the club and went from there. Me 25, her 39. I balanced it by having a gf who's 13 years younger recently.
Edit: the two relationships are nearly 20 years apart, I wasn't dating a 12-year-old.
#12
40 with a 28-year-old girlfriend was fun. We met at work and hit it off, but after trying a relationship, we were just too far apart mentally.
I don't want a partner I have to explain everything to feeling like I'm being overbearing, but they're all, 'No, that's fine, tell me what to do.' I want someone to tell me what to do and maybe have a little argument now and then if we dont agree.
#13
I was 20 and she was 49. I was hanging out at a bar when she walked in. She recognized some of the regulars, and I did too. We struck up a conversation and surprisingly found we had a lot in common. We dated for a few weeks, but then it just fizzled out.
#15
He was a regular at the place I worked at. He impressed me with things that people my age didn’t have just yet. Now that I am looking back - how can a grown man in his 50s go for a teenager… Never again.
#16
I was 22 she was late 50s. We met at work. I liked her smile and long hair. She liked that I wasn't her husband.
#17
When I was 17 I slept with the woman who worked at car dealership I bought my first car at. She was 31 n married at that time, which I didn’t know. She was living with a friend n we were kinda seeing each other. Then one day there was brand new man’s watch in her room which was clearly a gift she was gonna give to someone. Stupidly I thought it might be me but she explained to me that it was for her husband they were trying to reconcile n so we can’t see each other anymore. Good cuz I hated that stupid watch anyway.
#18
I went for social dance congress (salsa) in her city, met randomly via a common acquaintance, started dating in a month a married a year later. We have two great kids, she is around 20 years younger. It just happened...
#19
I was 20 and he was 58. We hit it off right away chatting online. Met in person after a month of talking, moved in together after 3 years, and got engaged after 5. We’ve been together for 6 years now and I can’t imagine anyone making me happier than he does.
#20
Work. I was 22 and he was 37. Trash experience overall. He was a predator and I didn't know at the time.
#21
I met him at work and I had a crush on him and would flirt with him here and there. Went to a party with other coworkers and they knew I liked him and tried inviting him to said party, but then his friend that was texting him told me his age which he lied saying he was 25 and I guess told him I was older too, so we went on first date and learned about each others ages I was 19 and he was 34 by then we’d fallen for each other, and were together for 5 years.
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