“Biggest Cheater Ever”: 30 Honest Age Gap Relationship Stories Shared By People Online

Met at work. She was 38, I was 24. Both female. Thought she was straight, so did she. We were friends, I always fancied her but didn’t know she felt the same. Only took 3.5 years before she told me how she felt and we’ve been together ever since! Best relationship I’ve ever had, she’s my best mate and the most wonderful person I’ve ever met. Age doesn’t really come into it, we’re just people who fell in love!

I’m 28 and she’s 42. We’re having a baby girl next month, together 2 years in January. She is the greatest partner I could have ever imagined and she came with 3 kids that all love me.

Im 57 and hes 39. He found me online. 18 years later still going strong.

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

My boyfriend was 17 years younger, I was 50 at the time. He was and is one of the sweetest humans I've ever met. He was getting over a divorce when we met. 


I had a small business, a home, a community I loved. He wanted to move back to the Colorado mountains and live in a cabin. He wanted to marry me and we would be so happy in the wilderness.


Sigh. No. We text regularly  still.  He always tells me he still loves me. 


TBH, I love him too.  But a woman in her 70s is not a good match for a healthy man in his 50s, and I'm smart enough to know that. .

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).

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.

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.

I went to see his band play with a friend of mine and she made us go up and talk to them. He definitely did not know how young I was (dark dive bar, I had a lot of makeup on and I'm tall). We added each other on facebook and then met up a few times and got along very very well. I made sure he wasn't a f*****g creep. Now we're married :) 11 year difference.

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.

I had a fantastic relationship with a woman a little over twenty years older than me when I was in my early to mid 20's.

She was the older sister of an older colleague that I'd become mates with in my first job out of uni.

I met her out with him one night and we clicked, and that night it started.

I was reasonably fresh out of what had a been a taxing relationship - my first serious gf, who I'd been with for most of uni, and this really wonderful lady was very keen to get out of a dead bedroom marriage on its last legs.

We saw each other sporadically, and when opportunity allowed over the next two or three years, until I took up with another serious gf. Subsequently we still saw each other occasionally at social occasions over the next 15 years before losing touch a bit, she became less healthy in her 60s and was out less. I still heard of her from her brother who I remained good friends with, and always asked after her, as she did me, and well wishes were always exchanged through him both ways.

I'm 54 now, and sadly she died of cancer a couple of years ago. I wish I'd seen her again before she passed.

We always had a very special place in our hearts for each other.

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.

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.

We hit it off through a book club. Age didn’t matter because we were both passionate about the same stories and ideas.

When I was in high school a friend’s mom got divorced. We had a brief thing. It shouldn’t have happened and if anyone had found out she would have been in a lot of legal trouble. It had a profound effect on my ability to have normal relationships that includes both sexual and just friends in general…..I leaned to hide relationships and to not feel comfortable talking about them. It also f****d up my relationship with my family because they didn’t know and didnt understand my f****d up behavior at that time. It also has led to me mostly having inappropriate or in other ways poor choices in partners.

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.

Was an ex-coworker. did some computer work for her one day. that day turned into my only “like the start of a p**no” hookup. was working on her macbook and she mentioned her photos app was very slow. open up app, tons of nsfw selfies. i look away and she just smiles and says shes been having some fun recently. decide to be brave, “so. you wanna hook up?”. narrator: “she did in fact want to hookup”

was about 10 yrs older but damn she kept in shape and much fun was had for a few months.

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.

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.

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.