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14 People Share What's It's Really Like to Have An Ex Who Is Now Their In-Law

Redbook logo Redbook 2017-03-27 Caralynn Lippo

Breakups are hard. Whether it's the awkwardness of ending things with a casual fling or the heartbreak of getting dumped by someone you legitimately love, it sucks. But that pain and discomfort is on an entirely different level when your ex moves on - with your sibling.

Just ask these Redditors, who revealed what it's like to have an ex for a brother- or sister-in-law. From surprisingly chill outcomes to palpable tension at family events, here are some of the most noteworthy responses.

1. "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 the manwh*re, 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 man wh*re 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." -Hobohooker

2. "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. I am a guy, my ex is bisexual, and my sister is 10/10 gay." -Fumbletongue

3. "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 name, right? Like TaylorSchwiftyAMA III. 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 TaylorSchwiftyAMA III... ergo, my nephew has my name. My ex-GF now shrieks my name every time Lil' Taylor gets into sh*t. That is not how I wanted that break-up to go at all." -TaylorSchwiftyAMA

4. "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 when 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." -Munchlax_1147

5. "Went on a few dates with a girl, we hooked up in my car, and then I found out she had a boyfriend, so f**k that. A few weeks later, a friend of mine introduces me to a girl he's dating - it's her sister. Small world. The friend turns out to be a big asshole, but me and the sister start dating. Kinda weird at first, but she's amazing. I 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 cuz we're family now. I see things I've seen before, but definitely should not be seeing now. GF doesn't seem to mind, guess she's past it. Eight years go by, and 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

6. "Currently dating the 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 I ignored it because I really liked the whole family and didn't want to do anything to f**k that up. I 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 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 so that's a win. Maybe I'll update this post in a few years." -wildcat2015

7. "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

8. "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's 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." -Mystory9998

14 People Share What's It's Really Like to Have An Ex Who Is Now Their In-Law © Getty 14 People Share What's It's Really Like to Have An Ex Who Is Now Their In-Law

9. "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

10. "Whenever people ask how me 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 having repeated casual sex with his twin brother (R) and R's girlfriend (who I met off a swinger site). This turned into a really dramatic six month long affair with R cheating on his (previously mentioned) GF 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 sh*tty 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 GF 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 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 R's GF, who is still with him, because it's really sh*tty 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)." -SuperSecretSociopath

11. "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 (yeah, you heard right) 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 hair style, and uniforms don't help. After about three 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 two kids. The ex also has two 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 about how I got the better deal. I still talk to her a few times a week. No one thinks it's weird." -thebigdustin

12. "My older brother is currently engaged to an ex-GF 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 he 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 when we were kids. It's caused me a lot of anxiety. I've been seeing a therapist, and 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 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. It's sad - he gave me a half-assed apology once, mostly because my dad forced him to. Maybe I'm just a dick, but I refuse to celebrate their relationship, because it isn't some fairy tale love story. My brother's approaching 30, and I'm sure as his friends get married he's feeling pressure. It's all sh*tty, 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." -Abtino11

13. "I originally started talking to my husband because he was attempting to pursue my sister, and I thought she could really use a man, so I was attempting to help. They went on two dates, I think, before she decided she didn't like him. So we kept talking, fell in love, and now we're married. My sister thankfully skipped her sloppy seconds toast at the wedding." -sadwhalenoises

14. "I'm the ex. I don't know how they feel, because we haven't spoken since they called to tell me they were dating my ex. They've since married and had a kid. I've tried to reach out and let them know I'm not upset about it, but I get no response. It caused a split in the family." -HasBenThere

Answers have been lightly edited for spelling and grammar.

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