Just like romantic relationships, friendships come with their own set of red flags. If a friend’s gaslighting you: red flag. Talking behind your back? Nope, absolutely not. But hooking up with a friend’s ex or, worse, their dad? That’s a hard pass and a one-way ticket to chaos.
So when someone online asked, “Have you ever slept with your friend’s SO, ex, or even their parent? How did it happen, and what came next?”—well, the internet did not disappoint. From explosive fallouts to shocking romance plots you’d expect in a soap opera, the responses were wild. Some were full-blown heartbreak stories, others spiraled into emotional wreckage, and a few? Let’s just say nobody involved came out completely clean.
#1
Obvious throw away and I’m sure this will get buried but anyways.
Met this guy at the beginning of college. Dated all through college. Anyways my boyfriend at the time (the son) became super controlling, manipulative and borderline a*****e, which all came to a head when his parents years long divorce was finalized.
Dumped the boyfriend, he moved out of state and the dad still lived close by. Stayed in contact with the dad and many other people from his family. Eventually the dad asked how my dating life was an I took it as an opportunity to complain about how I was having a hard time finding people who I had sexual chemistry with. Turned into a conversation about kinks and eventually (over a few months) the tension just kept building. To be blunt. We were both h***y, lonely and knew the other person was into the same things so we started a fwb type relationship. Helped that the dad was young and aged wonderfully.
Eventually it ended, on good terms. We both met other people. We both pushed the other to date other people. Find something long term and more fulfilling then cheep s*x.
From what I know no one knows, I never told and he didn’t either. We were just lonely, needed some s*x and wasn’t about to have casual s*x with randoms. Might as well be someone you know that will be happy for you once you find the right relationship. Ya it was slutty of me and maybe I’ll regret it in the future but at the time it was amazing s*x with a good looking person I trusted.
And and FYI the dad never hit on me while I dated the son. To my knowledge anyways.
Met this guy at the beginning of college. Dated all through college. Anyways my boyfriend at the time (the son) became super controlling, manipulative and borderline a*****e, which all came to a head when his parents years long divorce was finalized.
Dumped the boyfriend, he moved out of state and the dad still lived close by. Stayed in contact with the dad and many other people from his family. Eventually the dad asked how my dating life was an I took it as an opportunity to complain about how I was having a hard time finding people who I had sexual chemistry with. Turned into a conversation about kinks and eventually (over a few months) the tension just kept building. To be blunt. We were both h***y, lonely and knew the other person was into the same things so we started a fwb type relationship. Helped that the dad was young and aged wonderfully.
Eventually it ended, on good terms. We both met other people. We both pushed the other to date other people. Find something long term and more fulfilling then cheep s*x.
From what I know no one knows, I never told and he didn’t either. We were just lonely, needed some s*x and wasn’t about to have casual s*x with randoms. Might as well be someone you know that will be happy for you once you find the right relationship. Ya it was slutty of me and maybe I’ll regret it in the future but at the time it was amazing s*x with a good looking person I trusted.
And and FYI the dad never hit on me while I dated the son. To my knowledge anyways.
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37points
#2
I slept with a childhood friend's dad while visiting my hometown. Long story short he's bi and divorced and I was browsing on a gay hookup app (it's a small countryside town so the only things to do are ketamine, s*x or leave), he messages me and he clearly doesn't recognise me because I don't look the same as I did a decade ago. I recognise him and the entire time i'm thinking "this is really weird" but i'm bored and he's relatively handsome and charming (as far as charming goes on Grindr lol) so I figure hey why not.
And hindsight is 20-20 because the s*x was fun but the entire time i'm thinking "this is my friend's dad he has literally driven me to school before". Just left an overall odd feeling.
My friend doesn't know and it's going to stay that way because we don't really talk whatsoever now and it'd be weird to just pop up like "your dad jackhammered my prostate and it was kinda weird".
And hindsight is 20-20 because the s*x was fun but the entire time i'm thinking "this is my friend's dad he has literally driven me to school before". Just left an overall odd feeling.
My friend doesn't know and it's going to stay that way because we don't really talk whatsoever now and it'd be weird to just pop up like "your dad jackhammered my prostate and it was kinda weird".
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24points
#3
Well I guess I’m late to the game... but anyway, I’m in a relationship with my friend’s dad. It’s been like 3ish years now? Obviously we have s*x. It started when my friend told me her dad was hiring at his small business. We met, I was hired, for a year there was nothing but professionalism between us (I was in another relationship that was gradually on the outs). Broke up with boyfriend of the time, boss man had become genuinely good company and was there for me in a non creepy way. Never hit on me or suggested anything. We would just stay up all night talking about everything. We’re both artists with some quirks so in the aftermath of a depressing breakup it was nice to find validation in another person sharing a certain type of worldview. One night he kept complaining about his shoulders hurting. I was thinking “wow, is this an attempt to flirt? Ok I’ll bite...” so I rubbed his shoulders a bit while we watched a movie and afterwards he said he was going to bed and I could sleep on the couch if I was too tired/tipsy to drive. For some reason, I did not like that option. I pretty much called him out, telling him he could at least invite me up to spoon. For a while it was just that, I’d spend the night in his bed but nothing would happen. Then we eventually made out one drunken evening, and a few months later started hooking up. It was kind of open ended and label free for a while, but now we live together and our dogs are best buds so life is pretty good. He is the best, kindest, most empathetic and brilliant person I know. He’s sleeping next to me right now and I love waking up next to him every morning. Even if sometimes it’s because his farts wake me up but waking up laughing is the best.
24points
You’ve probably heard the saying, “Friends are the family you choose for yourself.” And honestly, it makes sense: they’re the ones who show up with snacks when you’re heartbroken, hype you up before big moments, and laugh at your worst jokes just to make you feel seen. Good friends make life a little less chaotic and a whole lot more meaningful. They become your second family—not by blood, but by choice.
But let’s not pretend every friendship feels like a warm hug. Some friends are the emotional equivalent of a speed bump made of Legos. They discourage your dreams, roll their eyes when you share your goals, and somehow always make your good news about themselves. They’re the ones who disappear when you need support and magically reappear when they need something from you. If you’ve ever felt worse after talking to a “friend,” chances are, they’re not really one. And sometimes, the hardest part of adulting is realizing it’s time to walk away from the bad ones.
#4
I had an on-and-off affair with my friend's dad for almost 3 years. Started when I was 17 and he was... mid-40s, idk his exact age. Not proud of it. I'm a guy and he was married to a woman, so we kept it hush-hush for a lot of reasons. They lived down the street from my parents so that made it convenient I guess. This friend and I were never super close and as far as I know, no one ever found out. I broke it off when I was around 20 because the guilt finally caught up with me. About a year later he called me to tell me he was getting divorced because he found out his wife had cheated on him (couldn't help but laugh at the irony there). He wanted me to be a shoulder he could cry on (and probably wanted us to pick up where we left off) but I shut it down pretty quickly. I'm almost 30 now and haven't heard from him in years, but my parents still see him around town. Apparently he's openly gay now, so in spite of everything that happened between us, it still makes me happy that after all these years he's finally comfortable being himself.
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19points
#5
Super drunken college party.
I had recently had my heart broken, shattered. I was with friends and their larty and honestly not really in the mood but drank some anyway. Was hitting on, essentially telling a friend he had a free pass. He chose the younger, skinnier, sluttier girl.
I was too drunk to drive home, as were many people. Including friend's dad. Arrangements worked out that we bunked together. Super drunk me is always handsy and down for s*x, and friend's dad figured it would be a good time.
For the record, I did not feel taken advantage of, he did not pressure me in any way, I initiated everything, he stopped and asked multiple times if I was sure/ok/wanted to continue. He was very respectful and it was not a bad experience in any way.
Next morning he and I were the first to wake, I started cleaning my friends' house. Eventually everyone woke up, we went out for breakfast, friend's dad picked up the tab. We all hung out the next day and I helped finish cleaning the house. We all said goodbye to friend's dad as he was just in town visiting. We all continued on with life. Saw him one more time at friends wedding.
Hung out with others who were at the oarty and also talked with friend's dad. One person knew we slept together because friends dad told him, one knew because I told him. It wasn't ever made a big deal.
I had recently had my heart broken, shattered. I was with friends and their larty and honestly not really in the mood but drank some anyway. Was hitting on, essentially telling a friend he had a free pass. He chose the younger, skinnier, sluttier girl.
I was too drunk to drive home, as were many people. Including friend's dad. Arrangements worked out that we bunked together. Super drunk me is always handsy and down for s*x, and friend's dad figured it would be a good time.
For the record, I did not feel taken advantage of, he did not pressure me in any way, I initiated everything, he stopped and asked multiple times if I was sure/ok/wanted to continue. He was very respectful and it was not a bad experience in any way.
Next morning he and I were the first to wake, I started cleaning my friends' house. Eventually everyone woke up, we went out for breakfast, friend's dad picked up the tab. We all hung out the next day and I helped finish cleaning the house. We all said goodbye to friend's dad as he was just in town visiting. We all continued on with life. Saw him one more time at friends wedding.
Hung out with others who were at the oarty and also talked with friend's dad. One person knew we slept together because friends dad told him, one knew because I told him. It wasn't ever made a big deal.
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16points
#6
Yeah. I’m a guy and I hooked up with my ex best friends dad. Friend and I were super close but when I came out as gay he started being distant and we grew apart sadly. I’d know this friend for years since I was a teenager but by this point I was early 20s. I was always at his dads house when I visited him and his dad and I always chatted. One time we were talking about taking a trip and he said if he ever went there again he would hit me up. So a few months later he told me he was gonna be there for a week and he had a hotel room I could stay in. To be clear I wasn’t sure he was interested and he didn’t even know I was gay at this point but I kinda felt a vibe and we had always hit it off. I said sure and flew out there. When I got there, there was only one bed in the hotel room. So I was like sure whatever. A couple drunken nights later we were sleeping and I kinda snuggled up to him. And then it was just on.com. To be honest it was super hot and a long time fantasy. We hooked up the whole week I was there and it was one of the best trips. I felt kinda guilty but said friend had been my best friend and then shunned me for being gay after knowing me most my life so f**k that guy.
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15points
And while it’s tough to know someone’s true nature right off the bat, there are a few red flags that quietly wave from the start. One major one? You can’t be yourself around them. If you’re constantly walking on eggshells or shrinking parts of yourself to keep them comfortable, that’s a problem.
Maybe they roll their eyes when you gush about sports or scoff when you dance like nobody’s watching. These kinds of “friends” don’t just dim your sparkle, they slowly steal the joy from things you love. And honestly, who needs that kind of energy?
#7
When I was 20, I got accepted to university in Canada (I’m a French guy) and my mum put together a BBQ to celebrate it with my best friends, among which was my actual best friend (girl my age), who lived far so she would stay the night.
My mum and dad were already getting divorced and sleeping in separate rooms back then, so there was no doubt they will ever get back to normalcy in terms of their relationship.
After most people left (and I was drunking my way around talking about Canada with another friend), my (now former) best friend and my dad made sure my mum went to bed and carried on drinking together.
All I remember after is me trying to figure out where the hell my friend was in the morning as the guest room was empty. It took so much fighting denial to realize she had been sleeping with my dad all night... Mum was destroyed, so was I, they both denied it and said they « just talked ».
I still cannot believe this happened but with retrospective my dad has been such a c**p dad to his kids and wife and that friend has not been nice to me either.
EDIT: wow, I did not expect this story to go that far! Thank you for the awards and the heartwarming comments. First time sharing something that personal so publicly but I am glad I did!
My mum and dad were already getting divorced and sleeping in separate rooms back then, so there was no doubt they will ever get back to normalcy in terms of their relationship.
After most people left (and I was drunking my way around talking about Canada with another friend), my (now former) best friend and my dad made sure my mum went to bed and carried on drinking together.
All I remember after is me trying to figure out where the hell my friend was in the morning as the guest room was empty. It took so much fighting denial to realize she had been sleeping with my dad all night... Mum was destroyed, so was I, they both denied it and said they « just talked ».
I still cannot believe this happened but with retrospective my dad has been such a c**p dad to his kids and wife and that friend has not been nice to me either.
EDIT: wow, I did not expect this story to go that far! Thank you for the awards and the heartwarming comments. First time sharing something that personal so publicly but I am glad I did!
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13points
#8
Ah Jesus christ why...alright, so it was this past summer. My buddy had a storage unit. I'm a guy, he's a guy. We were fixing something in his storage unit one weekend and I had left some tools there. He wouldn't give them back after weeks of asking so I went to his house where he lives with his parents. His dad opens the door and I am him if I can see his son.
I go downstairs, this kid is passed out from drinking all night and ripping bongs. Useless. I tell his dad I have tools to grab from the storage unit (its a family storage unit).
Let me break in here and say I'm gay, this father knows I'm gay, he's also very religious.
So he's gives me the key to the unit and whispers "ill meet you there" and I was like ok. Whatever.
I drive to the storage unit, grab my tools and see him pull in. Were talking and talking and he get onto the topic how he has always wanted to try new things.....ummmm. he closes the storage unit door while we are both inside and im like accepting my fate here. Hes telling me how he's always wanted to be f****d but has been afraid to come out about it and simply asked, "are you able to help me with that?"
I was flabbergasted. BUT this guy is.....so hot. I have had fantasies about this i swear to God and its literally happening. I said sure and we went at it.
We wrapped up, he said thank you and I havnt talked to him since. Soooooo weird. But it was a legit dream come true
Edit grammar.
I go downstairs, this kid is passed out from drinking all night and ripping bongs. Useless. I tell his dad I have tools to grab from the storage unit (its a family storage unit).
Let me break in here and say I'm gay, this father knows I'm gay, he's also very religious.
So he's gives me the key to the unit and whispers "ill meet you there" and I was like ok. Whatever.
I drive to the storage unit, grab my tools and see him pull in. Were talking and talking and he get onto the topic how he has always wanted to try new things.....ummmm. he closes the storage unit door while we are both inside and im like accepting my fate here. Hes telling me how he's always wanted to be f****d but has been afraid to come out about it and simply asked, "are you able to help me with that?"
I was flabbergasted. BUT this guy is.....so hot. I have had fantasies about this i swear to God and its literally happening. I said sure and we went at it.
We wrapped up, he said thank you and I havnt talked to him since. Soooooo weird. But it was a legit dream come true
Edit grammar.
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13points
#9
A good friend of mine had this happen to her back in high school. She caught her (also high school aged) boyfriend sexting her 40-something year old mother and it led to her mom and her step dad’s divorce. All while she was 17 years old.
She still has a strained relationship with her mom to this day, we are 25 now so this happened almost 10 years ago. I don’t think you can ever get over that kind of betrayal by your own mother..... I believe she still has a good relationship with her (now ex) step dad though.
Her mom is now dating a man her age, but she will always be a predator in my eyes that seduces her daughter’s boyfriend. So gross.
She still has a strained relationship with her mom to this day, we are 25 now so this happened almost 10 years ago. I don’t think you can ever get over that kind of betrayal by your own mother..... I believe she still has a good relationship with her (now ex) step dad though.
Her mom is now dating a man her age, but she will always be a predator in my eyes that seduces her daughter’s boyfriend. So gross.
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12points
Then there are the ultra-competitive ones who treat friendship like a never-ending contest. Got a promotion? They suddenly have bigger career news. Shared your new hobby? Oh, they’ve already mastered it. These folks don’t clap for your wins, they try to outshine them. It’s not about growing together, it’s about staying one step ahead of you. And let’s be honest, it’s exhausting. Friendships should feel safe and supportive, not like you’re constantly in a talent show audition. If your success makes them insecure, it’s worth asking: are they really your friend?
#10
Not the same, but my friends dad was released from prison and then was sending me DMs. He was in his late 30s, and he'd try to get me to meet up with him. I was 15. My friend never told me why his dad was in prison, but a few years ago I googled it and it turns out he was locked up for sexual contact with a minor. I was lucky I didn't meet up with him.
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11points
#11
Slept with my best friend’s stepdad. I was going through some years where I didn’t give a s**t about anything, but walking out of that hotel I couldn’t believe the choice I’d made and regretted it deeply. I fell out with my best friend soon after about something else, I don’t know if she knew.
I’ve changed for the better since, but it’s my biggest regret to date. I’m sorry Mel.
I’ve changed for the better since, but it’s my biggest regret to date. I’m sorry Mel.
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11points
#12
I had s*x with one of my best friends mom. It was Thanksgiving and I was driving her back home and she confessed that she didn't have s*x in years since she was a widow. I told her that I didn't have s*x in months since I was moving. We talked a bit more and we sorta flirted and once we got to her house, she asked me to come inside and we did the deed.
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10points
Some friends seem to exist just to bring you down, not lift you up. And no, we’re not talking about helpful, constructive feedback, the kind that helps you grow. We mean the ones who find fault in literally everything you do, just for the sake of it. You suggest a new restaurant, and if the food’s not great?
Suddenly, it’s all your fault. Try a new outfit? They’ll raise an eyebrow before you’ve even walked out the door. These folks don’t offer insights, they dish out judgment. Their words don’t guide you, they gut-punch your confidence. That’s not friendship, it’s emotional sabotage.
#13
I had s*x with a good friends mom. Looking back, it’s really messed up. She had been working on me for months. I was only 18. I’m ashamed of it, fortunately the friend never found out. But as an adult, I now look back at it and realize that I was in over my head and she should have known better.
Edit...
Wow everyone, I appreciate the sympathy. Let me just tell you a little more so you don’t worry about me.
Was I groomed, maybe looking back, I was. But I was certainly no virgin. The reason I feel ashamed of it is because it was my friend’s mom. I could have had her anytime and she offered pretty often. So one night (I decided) to take her up on it.
This doesn’t affect me today, probably never did an any deep way, except feeling like c**p because it was a betrayal of my friend.
But as an adult, I find her decisions disgusting. And as an adult, I realize that my 18 year old self didn’t know anything about life and rarely thought of anything beyond getting laid. I’m not hard on myself about it these days, but I was for several years.
Edit...
Wow everyone, I appreciate the sympathy. Let me just tell you a little more so you don’t worry about me.
Was I groomed, maybe looking back, I was. But I was certainly no virgin. The reason I feel ashamed of it is because it was my friend’s mom. I could have had her anytime and she offered pretty often. So one night (I decided) to take her up on it.
This doesn’t affect me today, probably never did an any deep way, except feeling like c**p because it was a betrayal of my friend.
But as an adult, I find her decisions disgusting. And as an adult, I realize that my 18 year old self didn’t know anything about life and rarely thought of anything beyond getting laid. I’m not hard on myself about it these days, but I was for several years.
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10points
#14
Okay so, when I was 19 and I was dating this guy, he lived alone with his dad. I used to stay over when my bf was working and anyway it just kinda happened. Then kinda happened two more times on other occasions. His dad was basically a twenty year older version of him, right down to body type and anatomy.
Eventually I told him what happened, but he said he was always doing that, which made me overthink everything about the both of them. Long story short, that relationship didn’t last very long after that confession. I just wanted out.
Eventually I told him what happened, but he said he was always doing that, which made me overthink everything about the both of them. Long story short, that relationship didn’t last very long after that confession. I just wanted out.
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10points
#15
Interesting that the top twenty or so comments are younger male with older female (and one older male). Is that really that much more common, or is it more that young men like to brag about it while a woman feels shame for hooking up with a dad?
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9points
Some friends treat hangouts like they’re directing a movie and you’re just an extra. They want to decide everything: where you go, who joins, what’s on the menu, and even how long you stay. Your opinions?
Apparently not part of the script. At first, it might seem like they’re just being “organized,” but over time, you realize it’s all about control. There’s no room for your preferences or spontaneity. It’s their way or no way. That’s not a friendship, it’s a one-person dictatorship with snacks.
#16
Compared to all this s**t, my story is vanilla. Lmfao. Met a friend in College (we were 21 & 22), her dad was only 13 years older than we were. He was d**n fine. We flirted a few times, she knew, we didn’t make it obvious or gross. We ended up going on a few dates and had some fun. I never told her about the time I spent with her dad, don’t think she’d have cared to know one way or another. It was fun, he was fun. She and I still chat to this day, I’ve seen him once or twice. Nothing weird, everyone’s cool. Hot dad was hot 🤷🏻♀️.
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9points
#17
I met their dad first before I met them. Ex’s dad was my sugar daddy...and then I met the son
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9points
#18
A friend of mines mom basically hit on a number of us in the group and sadly it just became kind of a matter of time before one of us caved and it eventually happened. He saw it coming I feel bad for him.
Recently divorced mid 30s hot mom and a group of 18 yr olds. It wasnt me who did it.
Recently divorced mid 30s hot mom and a group of 18 yr olds. It wasnt me who did it.
8points
Some friends don’t just spill the tea, they brew an entire pot daily and serve it piping hot with a side of drama. And we’re not talking about a little harmless chitchat. They gossip non-stop, badmouth people they just hugged, and treat rumors like collectibles. Being around them feels like you’re walking through a minefield of negativity. At some point, you have to ask: are they your friend, or just a full-time broadcaster of bad vibes?
#19
Well, I was a h***y guy, and my friend's mom was... well, available, really. I'm not proud of it, it just kind of happened sometimes, and every time I felt shame. I don't know, like I was betraying my friend's trust? Worse thing was, she was actually a friend of my mom too, so I kinda saw her on a regular basis....
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8points
#20
A friend at school's mum was pretty hot. She was relatively young compared to most of our mums and his Dad was quite a bit older and absolutely minted. When we were young teenagers it was a bit of a running joke to give him s**t about his hot mum or how his Dad was her sugar daddy.
Fast forward to the end of sixth form (end of high school for US readers) when we were all 18 and he was having a party at his massive house to celebrate. Most people were outside getting drunk in the garden but I'd had a bad few months (family stuff) so wasn't really feeling it.
I decided to go and chill inside for a bit and in the kitchen I found his mum just drinking wine and looking forlornly out the window. I asked if she was ok and she pretty much unloaded her issues! She was miserable, she hated his Dad, she'd settled down without having a life first, felt trapped because she couldn't afford to leave, loved her kids etc.
I opened up about my issues too with my family and it actually felt good to talk to a relative stranger about it. I now realise I should have been seeing a therapist.
Anyway one thing led to another and she started making out with me. I didn't stop her. She then led me upstairs and the rest is history.
On the one hand, it was pretty awesome, she was smoking hot, I was pretty inexperienced, and she really knew how to communicate in the bedroom. On the other hand though, I knew I was betraying my friend (and f*****g up his parents' marriage) plus I could hear all my friends laughing and partying outside!
A few months later they got divorced and I understand she got a bit shafted in the deal because she'd cheated on him. I don't know if that was me or she did it with someone else too.
I am pretty ashamed about it but I also realise she was using me too. I was never under any illusion we had some special connection or anything but I can see she just wanted to f**k *someone* out of catharsis or frustration and maybe, subconsciously, to force the problems in the marriage into the daylight so she could finally get out.
TL;dr: Friend's mum was hot but miserable in her marriage. F****d 18yo me at a party to feel younger (and probably to sabotage her marriage).
Fast forward to the end of sixth form (end of high school for US readers) when we were all 18 and he was having a party at his massive house to celebrate. Most people were outside getting drunk in the garden but I'd had a bad few months (family stuff) so wasn't really feeling it.
I decided to go and chill inside for a bit and in the kitchen I found his mum just drinking wine and looking forlornly out the window. I asked if she was ok and she pretty much unloaded her issues! She was miserable, she hated his Dad, she'd settled down without having a life first, felt trapped because she couldn't afford to leave, loved her kids etc.
I opened up about my issues too with my family and it actually felt good to talk to a relative stranger about it. I now realise I should have been seeing a therapist.
Anyway one thing led to another and she started making out with me. I didn't stop her. She then led me upstairs and the rest is history.
On the one hand, it was pretty awesome, she was smoking hot, I was pretty inexperienced, and she really knew how to communicate in the bedroom. On the other hand though, I knew I was betraying my friend (and f*****g up his parents' marriage) plus I could hear all my friends laughing and partying outside!
A few months later they got divorced and I understand she got a bit shafted in the deal because she'd cheated on him. I don't know if that was me or she did it with someone else too.
I am pretty ashamed about it but I also realise she was using me too. I was never under any illusion we had some special connection or anything but I can see she just wanted to f**k *someone* out of catharsis or frustration and maybe, subconsciously, to force the problems in the marriage into the daylight so she could finally get out.
TL;dr: Friend's mum was hot but miserable in her marriage. F****d 18yo me at a party to feel younger (and probably to sabotage her marriage).
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8points