Dating your friend's ex can be a little uncomfortable. Dating your sibling's ex, well that's just plain awkward. Or it is? We went to AskReddit to find out the inside story of real-life people who have dated their sibling's ex. Let's see what they said.
(Content edited for clarity).
Grandma Should Have Listened To Her Sister
“My grandmother married my grandfather who had dated her sister previously. My great aunt said, verbatim ‘I couldn’t stand him.’ My grandmother should have taken her advice because he abandoned the family when his daughter was ten weeks old to run off with another woman.
Years after that, their daughter passed away in a hit-and-run and he was able to weasel his way into an insurance class-action lawsuit my grandmother was involved in and collect on his daughter’s name even though he hadn’t seen her in over twenty years. I never met him and he died about ten years ago, found in a hoarding situation, abandoned by his family because he of he was despicable, and his legs lost to uncontrolled diabetes.”
Some Sisters Never Get Over It
“My family is from India, all of my aunts and uncles had arranged marriages. My dad has seven siblings. My eldest aunt was engaged to a Canadian born Indian man, basically the jackpot back then. He flew over for the wedding, saw my youngest aunt, and asked to marry her instead. Since my grandparents were really poor and had already spent money for the wedding, they agreed.
My aunts haven’t spoken in 45 years. We didn’t think my youngest aunt would attend my grandpa’s funeral. She came two minutes before and sat in the back, causing a bit of a commotion. My eldest aunt decided to start screaming and throwing herself at the casket. Neither of them had seen my grandpa since he was diagnosed with Alzheimer’s eight years previously, and had been in the hospital for a year after a bout of pneumonia. My dad (who paid all the bills) was not pleased since he just wanted a quiet, dignified ceremony.
Now we haven’t spoken to them in eight years.”
Two For The Price Of One
“I’m a twin and my wife briefly dated my brother before me. It was comical and still a bit of a joke now, but nobody cares. Actually, at my wedding, I was up at the bar, and my wife and brother were still sitting at the head table. People started clinking their glasses, so my brother leaned in a kissed her on her cheek.”
When Your Stepmom and Aunt Are The Same Person
“My stepmom met my uncle back in the early ’80s. They dated for a while, and in 1986, she gave birth to a little boy. They never got married. A year or two later, they broke up, and the woman I called my ‘aunt’ was now dating my dad (my uncle’s younger brother). My dad was divorcing my mother when I was 3 because my mother caught my dad cheating with my ‘aunt,’ who was also her best friend.
My dad and ‘aunt’ dated for several years and got married when I was 7. Family functions were tense for the first few years, but they have been married for over 25 years now. So, I can’t hate that she made my dad happier than my mom did. The running joke was that she is AuntMom and her son (my step-brother) is my ‘brousin.’ We don’t tell that joke within earshot of my stepmom (aunt) though.”
Cheaters Never Change
“A really good friend of mine dated a guy who cheated on her with her sister. They broke things off for a few months, he apologized, then they decided to try again. A month in, she found out he was cheating again with the same sister. Turns out he got the sister pregnant. My friend really hated her sister and the thought of a baby being involved for a long time. Now the guy is no longer in the picture, she’s forgiven her sister, and she adores her nephew. I’m glad it worked out for her, but I don’t know if I’d be able to mend things after that.”
Twin Drama
“I’m a twin, and my twin brother is now engaged to my ex. Let me just say it was really weird at first. I had been on/off again with a particular girl for over two years, left for the summer job (working on native reservations, very little contact with the outside world for months at a time) and when I came back, the girl I was dating was dating my brother, and had been for almost 2 months. My brother and I had a huge fight. The fight was weird, and he spent most of it just trying to calm me down because I was so upset. I ended up packing all my belongings away and moving to a new city. I knew absolutely no one. I enrolled in college and started pretty much a new life. I didn’t talk to my twin brother or see him again for over a year. I missed Christmas and our birthday and avoided the whole family (who were entirely split on the morality of this weird situation he caused).
As a side note, I love college, and I love my life here. I’ve grown monumentally as a person, and it was the best thing that has happened to me. My brother, my ex, and myself are all just fine now. You just have to deal with it, catch the bright side of it all, and move on.”
Marrying Your Ex-Husband’s Brother Is A Non-Issue
“My mom was married to my dad’s older brother before she married my dad. My mom’s first marriage (to my uncle) didn’t work because they’re basically the same person and neither of them could deal with the annoying parts of themselves in another person. They didn’t have any children. They were only married for 2 years, and they were in their early 20’s. They’re much better off as friends and are friends to this day.
There was a lot of time between the marriages, about 8 years, so everyone had time to get over it. My dad and his brother are as close as they always have been. My grandmother is an absolute saint and has never, ever said a cross word about my mom. The only person who ever had a problem with it was my granddad, and he died 2 years before my mom married my dad. My granddad wasn’t pleasant to my mother after she divorced his oldest son (my uncle, and the golden child), and didn’t live long enough to see her marry his middle son. He was always drinking and cheated on my saintly grandmother, so who cares about that as far as I’m concerned. I didn’t find out about any of this until I was 12 years old. No one intentionally hid it from me, it was just such a non-issue for everyone that it never came up.”
Revenge Wasn’t The Best Medicine This Time
“Years ago, I was dating this guy and we got engaged. He had a brother who was dating this girl. A few months after we got engaged, my boyfriend ended things. Shortly after, the brother’s girlfriend broke up with the brother, and my ex and the girlfriend started hanging out and talking a lot. I was convinced he broke up with me to date her, even though he denied it. Eventually, they did start dating.
His brother started texting me to talk about how they left us to be together and how much it hurt. Eventually, he got around to the point of trying to get me to hook up with him. I kept refusing but eventually agreed to hang out with him. We didn’t go all the way, but we did make out. I was young and hurt, and I knew what I was doing wasn’t right, but I just wanted to hurt him back and I knew that would do it. I never hung out with the brother again, but he would text me occasionally trying to get me to sleep with him, though I didn’t ever want to. Months later, my ex and I started talking again, and I disclosed to him what I had done. He was so upset but got over it eventually and we actually got married.
We never talked about it again, and I’ve never talked to the brother about it. All his family knows, but they’ve never mentioned anything to me. It almost feels like it never happened because it hasn’t ever been acknowledged by anyone; sometimes I even forget about it. Things are kind of awkward when I’m around the brother, but not so much that we can’t be around each other. He only gives me a weird side hug when he greets me and has never tried to strike up a conversation with me like he did before. One thing that is unfortunate is he’s now married, and I’m 99.999% sure his wife doesn’t know anything about it. I’m super close with her, and I know if she knew she wouldn’t like me at all.”
When Uncle Is a Better Dad Than Dad
“My mom married my dad, had me and my sister, then got divorced when I was 8. A year or so later, my mom started dating my dad’s brother (my uncle). He moved in with us, and eventually, they got married (I was probably 20 at that point). My uncle has been my stepdad longer than he was my uncle. My cousins are also my step-siblings, but we still refer to them as cousins, though we refer to my uncle as my stepdad. However, their kids refer to my mom as grandma. It’s all confusing, but we never really questioned it. My stepdad has been there and has done more in raising my sister and I than my dad has. My mom and he go to our family dinners and holidays along with my dad and stepmom. It’s just… accepted I guess.”
The Tale Of Two Brothers
“So, my husband ‘Bill’ and I have been together for a bit over five years. I met Bill through his younger brother ‘Bob.’ Bob and I had been friends for almost two years and dated off and on through that. It wasn’t anything serious, we were young, and Bob was a womanizer and not always the nicest guy.
Anyway, Bill and I ended up dating, and then got married. Pretty much no one in his family cared, other than Bob, who held a grudge. Bob was pretty petty for a while and tried to sabotage things between his brother and me for the first year or so.
That brings us up to now. Bill and I aren’t doing too well. He cheated in the first year of marriage, and I got over it, but he never really did. It ended up in a dead bedroom situation, with me having the much higher libido. Divorce has been thrown around. Finally, we settled on staying together for the kid, and opening up the relationship with a ‘don’t ask don’t tell’ policy. Well lo and behold, Bob and I always got along okay romantically, and now he’s my on again, off again friends with benefits partner.”
Adopted Siblings Are Still Siblings
“I dated a girl for a while. It was nothing too serious; we were only together about a month. I met her parents, some siblings, and her dad really liked me. I helped her dad lay down tile, and we got along well. I’d heard that she had two other siblings who were on some retreat for the whole summer. It ended up not working out (all we had in common was church stuff), but we remained friendly.
About a month after, I start meeting this other girl, and we hit it off. The new girl had the same last name as the first girl but was a totally different ethnicity, so I didn’t think much of it. The new and first girl were almost exactly the same age.
I asked her on a date, and on the day of, I went to pick her up. When I got to the address, I did a double take. It was the same house as the first girl. Okay. I pulled up, and the first girl’s dad greets me. ‘Hey (Bob), this is crazy, but do you know a (New Girl Name)? I was supposed to meet her here.’
Turns out that new girl was the adopted sibling of the first girl and was on a retreat all summer. I didn’t realize on account of the drastic difference in skin color.
Anyway, the dad was super awesome about it (gave me a high five). I dated a new girl for awhile until I moved away for college.”
When One Sister Moves Away, Try The Next
“I dated my ex’s younger sister for a while, but eventually stopped because we were going in different directions in life.
I had dated the oldest for a few months, and we eventually decided to split up amicably because I wanted a more romantic and serious relationship, but she just wanted a chill one with less commitment. Eventually, that led to a rift before we ended it.
I was on good terms with all the family, so it was a bit hard telling them what happened, but I never really lost contact with them. It was awkward for a bit, but we got over it, especially when they needed help cleaning out their mom’s hoard of trash.
We lost contact for a while as school had ended up consuming both of us. A few months later, I noticed that I hadn’t seen my ex in a week or so, and then I saw her younger sister crying, so I was worried. After talking, I learned that she had gotten caught with some SoCo on school property and was expelled, so her parents decided to put her on a plane to an island that her relatives lived on so that she could go to school there.
I felt bad because her younger sister was pretty much an outcast except in one small group that didn’t have any classes with each other, so I invited her to hang around with my group. Eventually, we started talking in a personal chat which was mostly full of funny memes and general goings-on.
One day, she randomly asked if I wanted to hang out at their place for the day because her mom was getting lonely without my ex being there. Eventually, I started hanging there more and more often, helping where I could and fixing things they couldn’t.
During this time, the younger sister and I had gotten pretty close, and one day this guy she liked had stood her up on a date. I lived close by and threw on a half decent shirt and walked up to the restaurant and ended up catching her before she left. I made a small scene apologizing to her. I just said that I’d forgotten to set the clock back and didn’t realize I was late. We had a nice time, and one thing led to another, and I ended up waking up in her bed the next morning.
We started officially dating not long after that, and wow was her sister mad. She had gotten it in her mind that I was doing to just to get back at her. Eventually, her mom talked her down and got her to leave me alone.
We ended up dating for a few years, but we ended up splitting because my dreams were simply incompatible with hers.”
True Love Will Find A Way
“I dated a girl for a summer while in college, and in the process was hanging around with many of her friends and her older sister. The older sister and I got along really well and very much liked each other. At the end of the summer, the girl I was dating moved away, so we had a very mutual break up. A few months later, I needed a date for a party I was going to, so I called up my old girlfriend and asked her if it was ok if I invited her older sister, and she thought it would be a great idea because her sister ‘really really liked me.’ So I took her sister to the party, we dated some more, and eventually, we get married a few years later.
We have now been married for 20 years, and it has never been an issue with anyone. The sisters are still best friends, we all visit with each other a few times a year, in some ways, it is like that initial summer never happened (with the exception that every once in a while we joke about it).”
A Real Life Hamlet
“My mom married my uncle right after my dad died. It felt so gross. I truly hate that dude, and I hate her now too. Plus the circumstances of my dad’s death were really weird. He was totally healthy one day, and then the next he was dead. It’s driving me kind of crazy to be honest.”
Brother’s Leftovers
“I had a friend who would go after any girl that showed him the least bit of attention. It usually didn’t result in anything because he’s not the most level-headed or physically attractive person around, but he’s smart. His brother is roughly the same, so when he’d bring his girlfriends around, his brother would also hang around. Eventually, he’d get to know them, and when his brother split from his girlfriend, he would swoop in and pick them back up.
There have been times when he would bring his brother’s recent ex over and they would sleep together in the next room over. When his brother tried to say something about it, he would freak out. Again, he’s not level-headed, so he would just scream over and over about how they were consenting adults. He wasn’t wrong, but it’s still not a cool thing to do. It put a lot of strain on him and his brother’s relationship, and seeing how he could behave that way and not feel the least bit sorry made me distance myself from him.”
Fell In Love With Her Sister
“I went out with my sister-in-law twice. We went out Sunday night, and after, she didn’t return my calls. She didn’t seem interested. Anyway, Friday someone called with a rumor that she eloped with a friend of mine who said he wasn’t interested (asked him before I took her out). It’s not all that relevant, but my friend and I kind of grew up together. He was in a wheelchair.
They seemed happy, and maybe I dodged a bullet. The next year, I met her 18-year-old sister. I was 21. There was no instant attraction, but we liked each others’ conversation. Within three months, we knew we wanted the same things out of life, and I was crazy in love with her. It’s been almost 20 years now and the best of my life. My wife pushed me through school, an MBA, and I started my own company, and we’re comfortable.
Her sister divorced the guy she eloped with and re-married; she seems happy.
A few times a year, she comes down to visit for a week at a time, and it’s not too bad. It’s probably more weird for her.
My wife and I are crazy about each other. My family is as crazy as hers, and she’s a great sport.”
Keep The Measurements Out Of This
“I had a pretty big crush on a guy, and we made out once or twice.
Ten years later, I ended up marrying his brother.
He asked me once when he was drinking if I had slept with his brother. I was really relieved that I could honestly say ‘no’ to that one.
I love his brother’s now-wife to pieces, also. His brother and I don’t talk about the past. We were kids, and then we grew up. We’re two different people now, and it isn’t really a big deal.
Although, sometimes I think about how hilariously awkward it is that I actually know some ‘intimate physical details’ about both brothers if you know what I mean.”
Heartbreak Doesn’t Last Forever
“My mother was in love with my dad’s older brother (my uncle) before meeting my dad. My uncle ended up dying in a tragic car accident back in Mexico. My mom and my dad’s family were devastated. Apparently, my mom cried hysterically at his wake and funeral, moaning about how much she loved him and how upset she was that he left her. My dad helped my mom find her way back to the US and ended up living with my dad along with several of his siblings. After a while, one thing led to another, then boom: I happened.
My dad’s family started to dislike her because they thought it was disrespectful to my uncle, who had passed away.”
Why Mourn When There’s Another Sister
“My grandfather’s mom died when he was around one year old, and her sister moved in to help with the kids. One thing led to another, and she married his father. So basically, my grandfather’s stepmom was also his aunt. And he has no memories of his biological mom. It went pretty well as far as I’ve heard, but the lack of conflict could be because one of the sibling’s death was the main reason it happened.”