Get Premium
Dark mode theme is available exclusively for premium users. Learn more about the benefits of subscribing.
No fees, cancel anytime.
Dark Mode 
No fees, cancel anytime 
“Biggest Cheater Ever”: 30 Honest Age Gap Relationship Stories Shared By People Online
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!
This post may include affiliate links.
#1
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!
#2
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.
#4
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
#5
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. .
#6
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).
#7
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.
#8
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.
#9
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.
#10
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.
#11
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.
#12
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.
#13
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.
#14
We hit it off through a book club. Age didn’t matter because we were both passionate about the same stories and ideas.
#15
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.
#16
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.
#17
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.
#18
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.
#19
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.
#20
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.
#21
Met him in a mental hospital, we were both patients. Obviously a very, very bad idea.
#22
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.
#23
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.
#24
I met her on AOL, i was 18 and she was 55. god DAMN was that fun, she had a nice apartment down by the lake, that was one of the most fun times in my life.
#25
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.
#26
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...
#27
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.
#28
Work. I was 22 and he was 37. Trash experience overall. He was a predator and I didn't know at the time.
#29
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.
#30
I was a youthful 21 and worked in a local pub. She was a 46 year old lady who drank in there on the weekends. She made it very well known that she fancied me and one day I had finished my shift at 4pm in time for an England football match and had ordered a pint at which point she came over and again told me she found me attractive, I thanked her and went out for a smoke.
I was outside having a smoke and she came out and asked for a lighter, I obliged. She lit her cigarette and kissed me and asked me to go back to hers. I thought about it for 10 seconds and agreed, I didn't even finish my pint and jumped in her car. We went back and I had the best BJ I've ever had (this was 2001) we showered together and fu***d like a couple of drugged up test bunnies.
Another time I just got accosted by someone on a works do and we sha**ed in the cellar of the venue we were drinking in. She knew the code on the keypad to open the cellar door. Bit chilly in there though, but naughty fun was had over the kegs. This lady was only older than me by a few years though
I'd go on but this isn't penthouse forum.
What do you think ?
Donkey boi 1 month ago
When I was 17 I looked early 20's. I dated a woman that looked (and I thought was) early 20's. Age never came up in conversation and I wasn't gonna torpedo myself! The night she wanted to step things up, we went back to her place, just as we were fondling on the sofa, we hear the front door shut. She says, 'S**t, my daughter must be home early!' Then in walks one of my classmates! All hell broke loose, but I did learn a few things that night. Such as; My date was 42 and was not interested in a relationship with "a child". Projectile vomiting is a real thing. My classmate had had a crush on me and had been asking her mother for advice about to approach me. Vomit moves down textured wallpaper at a very slow rate. Mothers should mention their children when dating. It can take a surprisingly long time for the smell of vomit hit your olfactory senses from the other side of the room. A mother in that position apparently has "no right to talk about what's appropriate" if the daughter swears.
KatSaidWhat 1 month ago
I was very young and VERY ignorant and didn't realise I was being groomed.
Koalafied to komment 1 month ago
When I was 25, I had a date through an app with a guy who maybe looked like 30ish, but would stay mysterious about his exact age. I liked him, though, and we were getting along fine, when he finally told me he's way over 40. I was surprised, not only because how wrong I was but also because he decided to hide it. I never saw him again, which was kind of sad, but I didn't like he wanted to keep it a secret until I was too much in love to run away.
ConstantlyJon 1 month ago
Our age gap isn't big like some of these, but my wife is 6 years older. When we got married I was 25 and she was 31. I've adopted her kids, so now on their birth certificates it has my as their dad and has my age on there at the time of birth. Weird my daughter out that it says I was 15 when she was born. When people do the math I tell them "yeah I wasn't cool enough in high school to be getting anyone pregnant."
Kraneia The Dancing Dryad 1 month ago
My "first" was 11 years older than me. I left because we were at different stages in our lives and different personalities (something I had tried to tell him at the beginning, but it went in one ear and out of the other!) I was barely 21 and he was 32. We loved each other very much and I still think of him, but we weren't compatible.
Jessica SpeLangm 1 month ago
I say the majority of these are fake stories and come from a person with a very active imagination.
The_Nicest_Misanthrope 1 month ago
Last guy I dated was 14 years older than me (his eldest daughter was 6 months older than me, in fact). That was definitely weird, but the relationship lasted 8 years total.
Graham Berry 1 month ago
This was refreshing. Yes age gap can be a red flag but primarily only when one party is under or very close to the legal limit. Most of the time correlation is not causation, if the older party is a s**t person or a good person they will be whether there is a age gap or not. The main thing that is important is that there is informed consent and that both parties are adults.
Amanda Fondaumiere 1 month ago
Sorry op I couldnt read more than a few of these, maybe too cynical. I did date someone 13 years older for three years. Turned out he was after my four year old and grooming the 2&3 year olds.
Layla Holston 1 month ago
My mom is 42 and my dad is 36. They met when i was less than a year old (Never knew my birth father) but i always say my dad is the old one.(jokingly)
Selena Wilson 1 month ago (edited)
He was 27, I was 33 (almost 34). That was 21 years ago. Still going strong.
Robert Beveridge 1 month ago
Dated a 46-year-old when I was 23. We were both poets who attended the same weekly reading series. Her son (who was six months older than I) did not approve.
Ovata Acronicta 1 month ago
I've been in two age gap relationships. First (and first serious relationship), my partner was 25 years my senior. I pursued him. He wasn't particularly a creep and didn't do a single thing indicating that he had a predatory bone in his body, he was just a stoner who never grew up, so when I did, it didn't work anymore (to clarify, I was a legal adult when I pursued him, but as I got into my mid 20s I outgrew him). For those who saw the ear pimple comment, that guy.
Ovata Acronicta 1 month ago
Second one, 30.5 year difference. Kind of a mutual interest, built up mostly by writing to each other. Was not the priority though, and when he was fairly absent from my support network when dealing with my grandma's declining health, and passing, I just kinda gave up on that. In a way I felt he was immature too. I'm not out here looking but I'd much rather someone nearer my age next time.
Load More Replies... Not-a-Clue (she/her) 1 month ago
My husband often teases me I should respect my elders. He's 34 older than me. (Days 😂)
Kaeda 1 month ago (edited)
There is a 29 year difference between my husband and I. I am 31 and my husband turned 60 earlier this year. He was married once before me (no kids) and he is my first marriage. Dated since I was 18, married when I was 22. We've been married almost ten years now and have two sweet children together (7yo and 3yo). He is my best friend and our relationship is so much stronger than anyone could even imagine. 💕
Donkey boi 1 month ago
When I was 17 I looked early 20's. I dated a woman that looked (and I thought was) early 20's. Age never came up in conversation and I wasn't gonna torpedo myself! The night she wanted to step things up, we went back to her place, just as we were fondling on the sofa, we hear the front door shut. She says, 'S**t, my daughter must be home early!' Then in walks one of my classmates! All hell broke loose, but I did learn a few things that night. Such as; My date was 42 and was not interested in a relationship with "a child". Projectile vomiting is a real thing. My classmate had had a crush on me and had been asking her mother for advice about to approach me. Vomit moves down textured wallpaper at a very slow rate. Mothers should mention their children when dating. It can take a surprisingly long time for the smell of vomit hit your olfactory senses from the other side of the room. A mother in that position apparently has "no right to talk about what's appropriate" if the daughter swears.
KatSaidWhat 1 month ago
I was very young and VERY ignorant and didn't realise I was being groomed.
Koalafied to komment 1 month ago
When I was 25, I had a date through an app with a guy who maybe looked like 30ish, but would stay mysterious about his exact age. I liked him, though, and we were getting along fine, when he finally told me he's way over 40. I was surprised, not only because how wrong I was but also because he decided to hide it. I never saw him again, which was kind of sad, but I didn't like he wanted to keep it a secret until I was too much in love to run away.
ConstantlyJon 1 month ago
Our age gap isn't big like some of these, but my wife is 6 years older. When we got married I was 25 and she was 31. I've adopted her kids, so now on their birth certificates it has my as their dad and has my age on there at the time of birth. Weird my daughter out that it says I was 15 when she was born. When people do the math I tell them "yeah I wasn't cool enough in high school to be getting anyone pregnant."
Kraneia The Dancing Dryad 1 month ago
My "first" was 11 years older than me. I left because we were at different stages in our lives and different personalities (something I had tried to tell him at the beginning, but it went in one ear and out of the other!) I was barely 21 and he was 32. We loved each other very much and I still think of him, but we weren't compatible.
Jessica SpeLangm 1 month ago
I say the majority of these are fake stories and come from a person with a very active imagination.
The_Nicest_Misanthrope 1 month ago
Last guy I dated was 14 years older than me (his eldest daughter was 6 months older than me, in fact). That was definitely weird, but the relationship lasted 8 years total.
Graham Berry 1 month ago
This was refreshing. Yes age gap can be a red flag but primarily only when one party is under or very close to the legal limit. Most of the time correlation is not causation, if the older party is a s**t person or a good person they will be whether there is a age gap or not. The main thing that is important is that there is informed consent and that both parties are adults.
Amanda Fondaumiere 1 month ago
Sorry op I couldnt read more than a few of these, maybe too cynical. I did date someone 13 years older for three years. Turned out he was after my four year old and grooming the 2&3 year olds.
Layla Holston 1 month ago
My mom is 42 and my dad is 36. They met when i was less than a year old (Never knew my birth father) but i always say my dad is the old one.(jokingly)
Selena Wilson 1 month ago (edited)
He was 27, I was 33 (almost 34). That was 21 years ago. Still going strong.
Robert Beveridge 1 month ago
Dated a 46-year-old when I was 23. We were both poets who attended the same weekly reading series. Her son (who was six months older than I) did not approve.
Ovata Acronicta 1 month ago
I've been in two age gap relationships. First (and first serious relationship), my partner was 25 years my senior. I pursued him. He wasn't particularly a creep and didn't do a single thing indicating that he had a predatory bone in his body, he was just a stoner who never grew up, so when I did, it didn't work anymore (to clarify, I was a legal adult when I pursued him, but as I got into my mid 20s I outgrew him). For those who saw the ear pimple comment, that guy.
Ovata Acronicta 1 month ago
Second one, 30.5 year difference. Kind of a mutual interest, built up mostly by writing to each other. Was not the priority though, and when he was fairly absent from my support network when dealing with my grandma's declining health, and passing, I just kinda gave up on that. In a way I felt he was immature too. I'm not out here looking but I'd much rather someone nearer my age next time.
Load More Replies... Not-a-Clue (she/her) 1 month ago
My husband often teases me I should respect my elders. He's 34 older than me. (Days 😂)
Kaeda 1 month ago (edited)
There is a 29 year difference between my husband and I. I am 31 and my husband turned 60 earlier this year. He was married once before me (no kids) and he is my first marriage. Dated since I was 18, married when I was 22. We've been married almost ten years now and have two sweet children together (7yo and 3yo). He is my best friend and our relationship is so much stronger than anyone could even imagine. 💕
You May Like Woman Runs Away From Date Only 20 Minutes In: “This Is My Mom” “Super Cute, Right?” She Dressed Up For A Date, Then His First Comment Shattered Everything Woman Refuses To Go Through Raising Kids Again, Single Dads On Dating App Get Defensive
Ilona Baliūnaitė
Lei RV
Mindaugas Balčiauskas
Related on Bored Panda
