People Who Married Or Dated Their Ex's Sibling Reveal How It Turned Out

‘It’s definitely weird because I see my ex sometimes at events.’

You can’t help who you fall in love with and for some families, that makes life a little complicated (to say the least).

People Who Married Or Dated Their Ex's Sibling Reveal How It Turned Out
Photo by Kevin Curtis on Unsplash

On Reddit, people who have married or dated their ex’s brother or sister have been sharing their stories.

There are also a few anecdotes from “the exes” and the “new partners” – and in some cases, it seems swapping partners was the best thing for everyone involved.

Well, they do say the path to true love doesn’t run smoothly.

“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.”

– kayjay25

“I went on a few dates with my wife’s sister a very long time ago. My sister-in-law is now married… to another woman. So, yeah, that worked out.”

– gamingtrent

“I’m currently in a serious relationship with my ex’s older sister. My current SO (significant other) and I were very close friends in high school and we would always set each other up with dates and stuff. She set me up with her younger sister and things were going great until she cheated on me. We broke up, and my SO was on my side of the whole thing and completely supportive. I was shocked to learn that she had feelings for me since second-year college.

“My girlfriend and I are going strong for two years now. It’s definitely weird because I see my ex sometimes at events or social gatherings, but we barely talk.”

– kingofstormandfire

“My wife dated my brother for a few months before we started dating. They took each other’s virginity and then she took mine when we started dating. It was definitely weird at first and my family would often crack jokes about it. We have been together for eight years now, married for 2.5 of them, and now it’s like it never happened.”

– Janders2124

“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 fuck that up.

“Broke up with ex, about a month later the sister is up at college 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. Ex doesn’t really talk to me when I’m around the house on breaks or whatever, but the family still really likes me.”

– wildcat2015

“I am a guy, my ex is bisexual and my sister is 10/10 gay. My sister has been dating an ex of mine for the last two years, and the ex 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, 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.”

– Fumbletongue

“My brother married my ex. My relationship with her didn’t last long (two months) and there was about two years between when we broke up and they started dating. It was a little weird at first but it’s really not anymore. It’d be weirder if they weren’t together. They’ve been married for a year now but together for about seven or eight years.”

– Munchlax_1147

“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-girlfriend is my sister-in-law…that is not how I wanted that break up to go at all. My wife is okay with things because we don’t live in the same city as my brother’s family and only see the rest of the family on holidays and special occasions.”

– TaylorSchwiftyAMA

“Went on a few dates with a girl, we hooked up in my car, and then I found out she had a boyfriend, so fuck that. A few weeks later, a friend of mine introduces me to a girl he’s dating – it’s her sister. Small world. Friend turns out to be a big asshole, 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. My girlfriend doesn’t seem to mind, I guess she’s past it. 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 – still weird.”

– sonofabee

“I went on a couple of dates with a guy, he turned out to be enough of a dick that I didn’t want to date him anymore but we had the same group of friends and saw each other often enough.

“I’m now married to his younger brother, my best friend. They don’t get along. We talked about everything once and agreed not to talk about it again unless something changes. He’s understanding, glad that we met through his brother, but would prefer not to think about it overly much. It helps that neither of us really speak to his brother and I don’t consider him family.”

– clericked

“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 had sex 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 themselves 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, my friends back home are in disbelief that she’s still involved in my family. I want to get to know my brother’s fiancé 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.”

– Abtino11

“I’m about to marry a girl whose (half) sister I originally dated. I dated them both in high school. My fiancee’s sister isn’t the smartest…it was not a meaningful relationship in my eyes, I did not have a car yet while dating her, so we didn’t hang out nearly enough. She was more into parties and alcohol than I, and eventually, we kinda agreed that it wasn’t going to work out. She has since estranged herself from most of her family, this means she doesn’t come up in conversation too much, but even if she does my SO is pretty chill about it.

“The fact I dated both of them definitely isn’t something she is proud to say, but we do occasionally tell people to see their reaction, which is generally hilarious.”

– Smurfymike

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