People Who Are Dating Their Ex's Sibling Share What It's Really Like
“She Doesn’t Want Me At Family Gatherings”
“I was engaged to a guy for four years that ended because of his inability to keep his little member 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 the cheater, 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 younger brother 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.”
“Still Weird”
“Went on a few dates with a girl, we hooked up in my car, and then I found out she had a boyfriend, so forget that. Few weeks later, friend of mine introduces me to a girl he’s dating – it’s her sister. Small world. Friend turns out to be a big prick, me and the sister start dating. Kinda weird at first, but she’s amazing. Meet her friends, turns out her 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. Still weird. 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. Girlfriend doesn’t seem to mind, guess she’s past it. 8 years go by, we’re getting married next week. Her sister has been the most helpful person planning our wedding. Really appreciate everything she’s done for us. Still weird.”
“My Dad Dated My Aunt First”
“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 had a substance abuse problem and worked on the corner. My mom hated her because of an incident where my aunt tried to win him back by dancing, removing her clothes and sitting on his lap — at my 1st birthday. The whole situation was a family secret until I was older.”
“I Dread The Day They Actually Get Married”
“Well, my older brother is currently engaged to an ex-girlfriend of mine. He lied to me for years about their relationship while I knew they were into each other. How did I know? When we were broken up (she cheated on me at college) but still talking we got into a fight, and during the fight, she told me she did it with my brother. I never told him I knew until a while later when he asked me if they could be together, and lied to my face when I asked if they had ever been physical.
We come from a very close family, I’ve always considered my brothers some of my best friends. But his actions speak for himself and his and my relationship is weaker than when he used to pick on me as children. It’s caused me a lot of anxiety, I’ve been seeing a therapist, I dread the day they actually get married if they’re going to pull the trigger. I’m embarrassed by it and my friends back home are in disbelief that she’s still involved in my family. I want to really get to know my brother’s fiancée but I already know so much about the type of person she is that I will never trust her. I still love my brother, but I haven’t looked up to him for a long time. It’s sad, he gave me a half-apology once mostly because my dad forced him to.
Maybe I’m just a prick, but I refuse to celebrate their relationship because it isn’t some fairy tale love story. My brother is approaching 30 and I’m sure as his friends get married he’s feeling the pressure. It’s awful, but I’ve got a life and career ahead of me and I know I won’t do anything like that to one of my friends and especially not my brother.”
“My Mother And Father Hate Each Other Passionately To This Day”
“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. 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 with gifts.
Spoiler alert, 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.”
“I Was Against Dating My Ex’s Twin Sister But She Pursued Me And I Caved”
“I started dating a girl after high school, we met while working at a grocery store. I heard through a friend of a friend she liked me so I asked her out. We dated for a little while but after about a month she ended up breaking up with me over the phone. I was really bummed because I liked her a lot.
Her twin sister also worked with us in the same department. It was super awkward at first because I would still confuse them for each other, both have the same initials, wore the same hairstyle, and uniforms don’t help. After about 3 months I heard from a friend of a friend that now the sister was asking around if I was still single. So a group of us went bowling and I ended up making out with her in the parking lot.
I was against dating her but she actually pursued me, so I caved and we started dating. At first, the ex wouldn’t make eye contact with me at work or speak to me. But after a while, the ex didn’t seem to mind. The sister didn’t seem to mind either, she didn’t date me out of spite or anything.
Fast forward 11 years we are now married with 2 kids. The ex also has 2 kids, from different fathers, been beaten a lot by her boyfriends, is always broke. No job. Can’t pay rent. Getting kicked out of her apartment. No car. Screams at her kids over the smallest thing. Constantly dumping them off on others so she can ‘clear her head.’
I look at her and say to myself, ‘That could have been you by my side, but I wasn’t good enough.’ I think sometimes how I got the better deal. I still talk to her a few times a week, no one thinks it’s weird.”
“I Think My Aunt Was The Vessel That Brought Them Together”
“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. 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 have always joked about it. As an adult, I asked my aunt the last time I saw her about it and she said she always knew my mom was right for my dad when she saw them interact the first time after they broke up. My parents have been married since the ’70s and still act like teenagers. I think my aunt was the vessel that brought them together.”
“Brother Uncles Are Married To Sister Aunts”
“My mom is the youngest of 5 with 4 older brothers. My oldest uncle, Ken, dated a woman named Vicky. They broke up. Then my second oldest uncle, Jim, started dating Vicky. This was awkward. But my Uncle Ken got over it by dating Vicky’s younger sister Linda.
So now my Uncle Ken is married to Linda, his ex-girlfriend’s (Vicky) sister. And my Uncle Jim is married to Vicky, my Uncle’s Ken’s ex and my Aunt Linda’s sister.
It’s ridiculous. No one cares, though. It was like 45 years ago. But it’s still pretty funny that brother uncles are married to sister aunts, one of whom dated both of my uncles.”
She Met A Couple On A Swinger Site Then Fell In Love With His Twin Brother
“Whenever people ask how I and my fiancé 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 casually fooling around with his twin brother (R) and R’s girlfriend (who I met off a swinger site). This turned into a really dramatic 6-month long affair with R cheating on his (previously mentioned) 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 R’s brother (D) 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 R, so we’d talk about it and he’d listen to all this drama. I was going through a really awful time in my life, and while things were very passionate and chaotic with R, I came to really value D’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 R. They are extremely similar in a lot of ways, but I still jokingly refer to D as the ‘good twin’ because he really is so thoughtful and insightful and great.
After everything blew up with R and his girlfriend finding out and being (rightfully) furious, I ended up spending even more time with D, and we fell in love, I moved in with him, and we’ve been together for 6 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 R’s girlfriend, who is still with him, because it’s really sucky 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 awhile. I’m sure that she still thinks that I’m only with D because I couldn’t have R (which isn’t true at all).”
“He Believes The Right People Are Together”
“I dated my current significant other’s brother for nearly 5 years. About 3 years into this relationship I found out about my now ex’s substance abuse issues. Tried to do the NA and AA thing with him, tried to support, tried to be there, but it was just slowly sucking me dry.
In the process, his brother (current SO) and nephew came to stay with us during his divorce from his ex-wife who was going through the exact same thing. I can’t explain it but during the time that they were with us, there was finally someone who saw and completely understood what was happening despite me trying to hide it. He knew what my life was like; he’d been living it. And I was at the point where I completely resented my ex, we had been living together but I was stuck trying to pay off my portion of things to get out while paying for everything to support both of us as his habit was taking over all of his financials.
I finally moved out and we kept in touch. Long story short we’re both so happy. It’s been 3 years and all the family has settled and fully understand. My ex went to rehab and is currently doing well and is understanding of how things played out. He believes the right people are together. We were a big portion of the support that got him there and he phones periodically to update and chat with us. I think he’s truly happy as I believe we are all good people working through the gray/difficult circumstances of life. He gets it; we are all honest with each other and time marches on.
I have never been in such a positive respectful relationship.
We both often forget the connection as we live so far away from his brother. We just talk about him like his brother and there are no issues around it. I think if you dwell on it you can find faults but we are just living and so so happy.”
“She’s Let It Slipped That She Loves Me When We Drink Together”
“The 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 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 hung 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.”
“My Ex Has Plans To Propose To My Sister”
“My sister has been dating an ex of mine for the last two years, and my ex has plans to propose to her at the end of the year. I am a guy, my ex is bi and my sister is 10/10 gay.
I love it. Not only is it a funny story to tell people, I remained very close friends with the 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.”
“The Family Still Really Likes Me So That’s A Win”
“Currently dating younger sister of an ex. 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 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.
I’ve casually brought up to the parents the topic of me dating 2 different daughters of theirs and neither really seemed bothered by it. The mom was actually happy because she missed me being around after I broke up with the ex, so go figure.”
“Michael’s Dad Doubles As His Uncle And His Stepmom Is His Aunt”
“This all happened before I was born, and I didn’t find out until I was in my 30’s.
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.”
The Grandfather Divorced Her To Marry Her Sister
“After my grandmother died (15 years before I was born) my grandfather got remarried for a few years before he divorced her to marry her sister. As a child I just knew the 2nd 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?’ Called him a liar and ran inside to tell on him to the adults inside, which included grandad, Aunty Beryl and grandma (3rd wife), and was met with an awkward response. By then everyone was pals but apparently the first few years after marriage number 3 wasn’t so chummy and involved some stalking & death threats.”
The Kids Call Their Biological Aunt ‘Mom’
“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.”
“I Am My Own Cousin”
“This happens in my family a lot.
My grandma married a guy and they had two daughters. We’ll call them Auntie A and Auntie B.
They got a divorce and she married my grandfather. They had two more daughters. We’ll call them Mom and Auntie C.
Grandma’s first husband then married grandma’s sister. They had a daughter. We’ll call her Cousin Sue.
So, Cousin Sue is my mom’s cousin. But she is my mom’s half sisters’ half sister, because Cousin Sue has the same dad as Auntie A and Auntie B.
There was a lot of animosity between my grandma and her sister who married her ex, and between my grandpa and the ex. My grandpa actually shot (did not kill) the ex at one point. Hey, it’s Wyoming. What can I say?
But wait, there’s more.
Cousin Sue grew up and married a guy. They had three kids. He died. She then married his brother, and had another kid. So now HER kids are sibling/cousins just like she is a sibling/cousin to two of her own half sisters.
Oh. And Auntie A married a guy. He had this brother. They introduced the brother to my mom. Yes, he is my dad. I am my own cousin.
This makes family gatherings uncomfortable since most of these people are divorced, but their kids still have to see the full sets of former in-laws.”
“My Mom Has Told Me That It Absolutely Devastated Her”
“My dad dated both my mom and my auntie.
My mom was head over heels in love with him from a very young age (unbeknownst to him of course). They’d gone on a date or two but had never become exclusive. My aunt showed an interest and he dropped my mom and started dating my aunt. My aunt knew my mom was hopelessly in love with him and still went for it. My mom has told me that it absolutely devastated her.
Eventually, he saw the light and realized my mom was the one for him. Dumped auntie, dated mom, proposed to her within the year.
He doesn’t like my aunt now. Not because of their past dating history, just because he thinks she’s nuts.”
He Didn’t Even Know They Existed Until He Overheard His Mom On The Phone
“My mom was previously married and had kids with my uncle, my dad’s cousin. She got to know the whole extended family very well since everyone lived in the same town (small town in Mexico) so that’s how she met my dad. It ended badly and she was too poor to move back with her family in another state so my dad’s family took her and her kids in. They lived houses down from her ex apparently so everyone saw each other often. I don’t know how long she was with them before her and my dad started seeing each other but it eventually happened.
In the beginning he treated the kids like his own – they were family after all. But after a while he started resenting them. Now he doesn’t like them being brought up. I didn’t even know they existed until I was probably 10 and that was just because I overheard my mom on the phone. They stayed in Mexico with their dad (my uncle), once my dad brought my mom and us (his actual kids), to the States.
No one ever understood why he flipped suddenly. But they all still live in the same town and my siblings visit my dad’s family (my grandpa and aunts) regularly. Nobody has a problem with it except for my dad.”
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