You never know who you’re going to fall in live with, but as a rule of thumb it’s good to keep things clean. Life is messy. What can you do?
Here are nineteen stories of people who ended up dating the sibling of their ex.
Many thanks to all the Redditors who responded. Check out more answers from the source at the end of this article!
1. Oh this is just mean!
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.
2. This is a bad move.
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 (who is also poor) orders top-shelf liquour.
3. Just a small crush!
My parents. My mom at 15 told her sister who was dating my dad at the time (3yr age difference) 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. 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 5 years. Mom’s family loved him. Aunt and mom are still great friends and talk have always joked about it.
As an adult I asked my aunt the last time I saw her (a few months ago) she said she always knew my mom was right when she saw them interact the first time after they (she and my dad) broke up. My parents have been married since the 70s. Still act like teenagers. I think my Aunt was the vessel that brought them together.
4. You never know what will happen…
I dated a woman for a couple of months many years ago, then broke up with her. However, she adored my family, so she continued to hang around with them – parents, brothers, etc. Fast forward 10 years, and she’s dating my younger brother, and I have to invite them TO MY WEDDING. Fast forward another year or two, and THEY get married… so now my ex-GF is my sister-in-law.
BUT WAIT. I am named after my father (like a junior)… so I should give my son the same, right? Except I decide not to – He can become his own man, instead of living in his dad’s/granddad’s shadow.
So THEY name their first son after my father and me… ergo my nephew has MY name. My ex-GF now shrieks my name every time Lil’ Taylor gets into something.
That is NOT how I wanted that break-up to go AT ALL.
My wife is OK with things, because we don’t live in the same city as my family and only see each other the rest of the family on holidays and special occasions. However, it doesn’t help stereotypes that we happen to be from a southern state. No Southerner wants to contribute to inbreeding jokes more than they absolutely have to.
5. But I’m too young!
My dad dated my aunt first. He proposed and she turned him down saying she was too young (18). Six months later my mom and him 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, just dated the sister as a second best, he said. Sad but they were married for 25 years before he passed.
However, I was raised believing my aunt was a drug addicted sex worker. My mom hated her because of an incident where my aunt tried to win him back…by stripping and sitting on his lap…at my 1st birthday. The whole situation was a family secret till I was older.
6. A win.
Currently dating younger sister of an ex. Ex and I were really close friends for years (met her through another ex actually) and tried dating for a while, it didn’t work because I couldn’t really stop seeing her as a friend only. Younger sister always crushed on me and was flirty but obviously ignored it because I really liked the whole family and didn’t want to do anything to mess that up.
Broke up with ex, 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 6 months later here we are. 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 maybe I’ll update this post in a few years.
7. “I understand why my father would have been in love with her…”
At the age of 29 I had the worst end to a relationship of my life. It absolutely crushed me. My sister had committed suicide earlier that year so I had already been unstable and this just set me over the edge.
My father, seeing me despondent, tried to console me. I think he was still trying to come to terms with the death of my sister or he might not have told me, I think he was worried what I might do. He shared the only similar experience he had, the one that got away: my aunt.
Some context here, of my mother’s five other siblings, this aunt is the one who is the closest with my mom. She is as close to a second mother as I have, and her children the closest thing I have to siblings left. She’s an amazing woman, kind and generous to a fault. If she has a weakness it’s that she’s too busy helping everyone else so gets overworked on occasion. I relate this both to say how close my family is to her and that I understand why my father would have been in love with her.
But I had no clue. For 29 years I had lived so close to this but been entirely unaware. I can see it now in his interactions with her, it still pains him but he covers it well. We haven’t discussed it since. None of my cousins know. I’m not sure my mother even knows. I get why my father shared it with me given my state at the time, but it really messes with my head to know about it now.
My great (x4) grandmother had three husbands, and the 2nd husband was the father of the 3rd. So when her second husband was murdered she married his son, and they raised 10 kids. 4 of whom where the bio siblings of husband number 3. (5 were his and one from 1st marriage)
Cecelia married Charles and they had one child before Charles drowned. Cecelia then married Richard, whom she had 4 more children with before he was murdered during the colonisation of my country (NZ).
Now, Richard had one more child from his first marriage called John. When Richard died John then married his step mother Cecelia, and had 5 children with her.
Cecelia had ten children all up, 1 from husband number 1, 4 from H2 (Johns half siblings) and 5 from H3 (John)
Age wise I’m not sure about H1, but H2 was around 15 years older than Cecelia, and H3 was 8 years younger, 19 to Cecelias 27 when they married.
I know all this because we’re having a family reunion next month and we’re making a short documentary on the family history.
9. Interesting bowling night.
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 afterwards.
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. All of us are on a bowling team together, too.
10. Just the old switcheroo.
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.
11. Interesting story.
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 drugs. I always see their marriage as one of convenience – she wanted a green card, he wanted a lawyer. (And some clean income didn’t hurt either.)
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 luxury 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 in gifts.
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.
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. Turned out my uncle is gay as a rainbow, that probably helps.
I dated my sister-in-law in high school and actually lost my virginity 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.
14. What’s the OTHER story?
I have a story for both of my wife’s sisters but I’ll just stick to one.
This 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 salty to 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 parents 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 slipped 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.
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.
16. Do they remember?
I fooled around with my boyfriend’s cousin when I was 16… 4 years before I met my now boyfriend. It was very, very odd upon meeting his family for the first time. Still have not verified with his cousin whether he remembers that I give him oral sex at that party.
17. What’s her problem?
I was engaged to a guy for four years that ended because of his inability to keep his little wang in his britches 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 fiance, I catch up with the older brother over drinks….cut to three years later and we are married. They never had a close relationship to begin with so it didn’t cause much trouble but the old fiance 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.
18. Good question…
This is only slightly related. My husband’s sister is dating a man, his sister is dating my brother… so three sets of brother/sisters all hooked up. At poker night my brother says “everyone look to the left and say I’m sorry for screwing your sister.”
Not quite sure how it’s going to play out at a breakup.
19. Bizarre indeed…
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, and gets out, 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 2 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.