What's the worst thing that can possibly happen when you split from your partner? Them going on to marry one of your siblings is probably near the top of that list. The mixed emotions and awkward family reunion moments could make even the most amicable breakups nasty.
**Below are stories of people whose ex-partners then went on to marry one of their siblings, and how things changed because of it. **
This makes for some awkward family drama.
“I can come close. I’m currently dating the younger sister of an ex.
My ex and I were really close friends for years and tried dating for a while. It didn’t work because I couldn’t really stop seeing her as a friend. Her younger sister always crushed on me and was flirty but I obviously ignored it because I really liked the whole family and didn’t want to do anything to mess that up.
I broke up with my ex, and about a month later, the sister is up at college like 1.5 hours from me. We’ve been texting and she says she wants me to visit. One thing led to another and six months later, here we are. My ex doesn’t really talk to me when I’m around the house on breaks or whatever, but the family still really likes me so that’s a win.”
Like tearing off a band-aid.
“My parents met when my mother was going to law school in the United States on a scholarship. My father, as far as I can tell, was making most of his income dealing illicit substances. I always see their marriage as one of convenience – she wanted a green card, he wanted a lawyer.
Fast forward ten years, they have three kids together, but fight constantly. My mother basically had two priorities – her children, and her career. She made that work, but there wasn’t much time left for the luxurious life my father seemed to want. Since both of my parents weren’t around that much, my mother’s younger sister – who rebelled against the family’s ideas of studying finance, and pursued a career in music instead – would spend her summers in the US, taking care of me and my younger siblings. And things were going well for her, too – she had a mysterious lover who would take her on lavish trips around the world, and shower her with gifts.
Spoiler: it was my dad. When my mother found out, she filed for divorce and moved back to Europe. My father and my aunt ended up marrying and having two kids of their own, who are now both my half-siblings and my cousins. My mother and father hate each other passionately to this day, and only see each other in court for the legal battle that has been going on for over twenty years now.
Weirdly enough, I still think it turned out for the best – both my parents are much happier than they ever were when they were together.”
It’s all in good humor!
“My wife was my best friend since grade school and for a brief period during our high school years, I dated her younger sister. We had a mutual break up after a few months and remained close. In college, my now-wife and I decided to take our friendship to the next level. We were married a few years later and now have two kids.
There is no awkwardness between any of us and the three of us frequently go out to dinner together. Everyone is lighthearted about it and my wife makes jokes all the time.”
Creating a rift between twins.
“An old friend of mine dated twins. She actually dated one and then cheated on him with his twin brother. They broke up and she dated the second twin for a long time.”
‘Parent Swap’, coming soon!
“I worked with a guy whose wife cheated on him and married the guy. The husband of the cheater consoled the wife of the cheating husband, and they ended up getting married.
Now the kids still have their original parents but in a different rotation. People are weird.”
Friendzoned her into another dimension.
“My wife’s sister is my age and used to be my best friend. We came close to hooking up a few times but I saw her as more of a good friend. I dated a ton of her close friends and eventually her little sister who I later married and had kids with.
As soon as I started dating my wife the friendship went super downhill.
She is always upset at both of us during brief meets but when we spend a few hours or more together we have a blast like the old times.
My wife has recently brought childhood books and notepads to our house for our kids from her parent’s house. I found several doodles with hearts with the older sister and my name in them.
I’ve pretty much messed around with every girl that she hangs out with. She’s heard all the intimate details about what I’ve done with all of them. I found out she was once madly in love with me. She’s let it slip that she loves me when we drink together as well. I now have a house and kids with her little sister and I feel horrible about everything.”
Lose your V-Card to one, marry the other.
“I dated my sister-in-law in high school and actually lost my V-card to her. We broke up and a few years after high school I ran into her older sister and we just hit it off.
We’ve been married for a little over a year now.”
The long road to love.
“My mom, at 15, told her sister, who was dating my dad at the time that she was going to marry my dad. My aunt laughed and said it’s a girl crush.
A few years later, my aunt and dad had broken up. My mom and dad are both attending the same college had a few classes together. She knew who he was, she seemed vaguely familiar to him. Eventually, they started to date, and get married after dating for five years. My mom’s family loved him. My aunt and mom are still great friends and have always joked about it.
I asked my aunt about it the last time I saw her. She said she always knew my mom was right when she saw them interact the first time after she and my dad broke up. My parents have been married since the 1970s. They still act like teenagers. I think my aunt was the vessel that brought them together.”
Riding other people’s dimes.
“My aunt is married to my mom’s ex. My mom isn’t too awkward about it, but my dad kind of hates the guy…though the guy is kind of a jerk, so I’m not even sure my dad hates him for that reason or even if my dad knows about that.
For example, my parents are always tight on money and when my dad offered to buy my aunt and uncle dinner, my uncle ordered top-shelf liquor.”
The family propaganda.
“My dad dated my aunt first. He proposed and she turned him down saying she was too young. Six months later, he and my mom got married.
My mom was freshly divorced from a physically abusive man and had two young boys to take care of so I think that had a lot to do with her motivation. My dad had a good job and had always had a thing for her, and just dated the sister as a second best, he said. They were married for 25 years before he passed.
However, I was raised believing my aunt was a terrible person. My mom hated her because of an incident where my aunt tried to win him back.”
He plays for the other team now.
“My mom used to date my dad’s younger brother. They broke up but remained on friendly terms and a few years later my dad got together with my mom. They all get along great.
As it turned out, my uncle is gay. That probably helped.”
These are the real lessons here.
“My physiology teacher tends to ramble on about her personal life instead of, you know, teaching us physiology. She dated a guy in college, and when stuff didn’t work out between them, her younger sister started dating and eventually married the guy.
They’re all still on good terms, and my teacher is fond of saying that her sister got the leftovers.”
Things were going juuuuust fine until she showed up…
“I was engaged to a guy for four years. It ended because of his inability to not cheat when he left the house. His older brother briefly lived with us during a job transition and we became pretty good friends. Shortly after leaving my ex, I catch up with the older brother over drinks and cut to three years later, we are married.
They never had a close relationship to begin with so it didn’t cause much trouble, but my ex started dating a woman recently who has a major issue with the situation. She doesn’t want me at family gatherings and refuses to let my niece and nephew stay with us anymore. We still haven’t figured out what her problem is but we haven’t lost any sleep over it.”
The kind of mess that cleans itself!
“I had an aunt Jennifer, who was married to Bob. Bob was a bit of a hound and apparently cheated on her quite a bit. Still, Bob and Jennifer decide to have a baby, and Michael was born. Bob ends up having an affair with Jennifer’s sister, Anna. Jennifer finds out about Bob and Anna, gets out of the marriage, and takes Michael with her.
Soon after, Jennifer starts dating my Uncle Rich. Rich and Bob know each other pretty well. They’re not good friends or anything, but they seem to run in the same circle. Things start going well for Rich and Jennifer, so within two years, they decide to move in together and get married. In the meantime, Bob and Anna are going pretty strong, so they shack up and get married around the same time.
Anna and Jennifer patch things up, and Jennifer forgives her. Over the years, things totally normalize, and they operate completely normally (at least on the surface), as Michael’s dad doubles as his uncle, and his stepmom is his aunt.
It was a very bizarre family dynamic, but it worked.”
How to Create a Confusing Family 101.
“There were two sisters who, during their teen years, both adored a nice young man named Bill. They didn’t like each other too much to begin with but this drove them even further apart.Then, he married one and had kids with her. The other sister married someone else, moved abroad, also had kids.
Some while later, ‘the other sister’ and Bill had an affair, and Bill and his wife ended up divorcing. He married ‘the other sister,’ rendering the first cousins now step-siblings.
The two sisters continue to hate each other all the more and Bill’s kids with his first wife call their biological aunt ‘Mom’.
Everyone seems to be happy jolly, but I’ve only seen from the perspective of the kids and the ‘other sister’. I’m sure had I known the entire view, it would be different.”
And henceforth, they were ACTUALLY sisters!
“My sister has been dating an ex of mine for the last two years, and she has plans to propose to her at the end of the year.
I love it. Not only is it a funny story to tell people, but I remained very close friends with my ex for years and I’ve been friends with her since we were fairly young. She was like a sister to me for years after we broke up, so it’s a bit of an interesting progression that she is now very likely to be my sister-in-law.”
Just some mild death threats, no worries!
“After my grandmother died, my grandfather got remarried for a few years before he divorced her to marry her sister. As a child, I just knew the second wife as Aunty Beryl. I didn’t know the whole sorry story until one day my cousin asked, ‘Did you know grandad used to be married to Aunty Beryl?’
I called him a liar and ran inside to tell on him to the adults inside and was met with an awkward response. By then, everyone was pals but apparently the first few years after marriage number three wasn’t so chummy and involved some stalking and death threats.”
I’d pay to show up to this episode of Jerry Springer.
“Whenever people ask how my fiancee and I met, we lie and say ‘the internet’, because the actual answer could be the plot of a Jerry Springer show.
The actual story is that we met because I was hooking up with his twin brother Robbie and Robbie’s girlfriend. This turned into a really dramatic six-month long affair with Robbie cheating on his girlfriend with me, her finding out and a whole lot of yelling and crying and drama.
Early on, while all this was going down and before the affair and the drama, I ended up meeting Robbie’s brother Doug on a night where we were all just hanging out. We hit it off and became really close friends, and as things got really complicated, he was one of the only people that knew about what was going on between me and Robbie, so we’d talk about it and he’d listen to all this drama. I was going through a really rough time in my life, and while things were very passionate and chaotic with Robbie, I came to really value Doug’s calmness and patience and empathy, and really fell in love with him as a human being, completely outside of what was going on with Robbie. They are extremely similar in a lot of ways, but I still jokingly refer to Doug as the ‘good twin’ because he really is so thoughtful and insightful and great.
After everything blew up with Robbie and his girlfriend finding out and being furious, I ended up spending even more time with Doug, and we fell in love, I moved in with him, and we’ve been together for six years. He’s amazingly chill about the whole thing and we just laugh about how it’s a super awkward way to have found each other. I genuinely feel bad for Robbie’s girlfriend, who is still with him, because it’s really rough for her to have to see ‘the other woman’ at family gatherings forever. We’ve moved past it, but it was really weird in group settings for a while. I’m sure that she still thinks that I’m only with Dough because I couldn’t have Robbie.”
Whole lifetime goes by, still weird.
“I went on a few dates with a girl. We hooked up in my car, and then I found out she had a boyfriend. A few weeks later, a friend of mine introduces me to a girl he’s dating and it’s her sister. Small world, right?
My friend turns out to be a big jerk, and the sister and I start dating. It’s kinda weird at first, but she’s amazing. I meet her friends, and it turns out that she and her sister hang in the same group. It gets awkward. We date a couple years, I start attending family events regularly. Her sister starts becoming more comfortable around me, sees me as a brother now. It’s still weird. Her sister wears comfy house clothes when I’m around because we’re family now. I see things I’ve seen before, but definitely should not be seeing now. My girlfriend doesn’t seem to mind, I guess she’s over it.
Now eight years go by, we’re getting married next week. Her sister has been the most helpful person planning our wedding. I really appreciate everything she’s done for us, but it’s still very weird.
Points have been edited for clarity.