24 People Who Dated Two Members Of The Same Family And Started A Whole Lot Of Drama

When it comes to romance, some lines are best not crossed. A good example? Dating two (or more!) members of the same family.

It’s a messy world, though, so sit back, relax, and enjoy these 24 wild stories about people who dated multiple members of the same family:

1."I was seeing my now husband at the same time I had a lil 'side hustle' going on with his son, who was 15 years younger than me. It was never going to be anything more than fun. My now husband has always suspected this, and his son knew about his Dad and me."

—anonymous

2."One of my best friends is married to a man her sister dated for years beforehand, and now they do not speak at all, and the entire family is broken. My friend actually got together with him while trying to arbitrate his relationship with her sister and says it 'just happened.'"

—anonymous

3."I started dating this guy in high school; we were very serious. We went to the same college and even got engaged. I graduated a year early and went to grad school on the other side of the country. I flew back home for my fiancé's graduation, and as soon as I stepped into the house, his best friend (who is also my stepbrother) pulled me aside and said my fiancé had gotten drunk at a party and slept with this girl. I was completely heartbroken, broke up with my fiancé, and got on a plane back home. Three months later, he started grad school in London, and I saw on our mutual friend's Instagram that he had gotten married to this girl he met when he moved. To say it calmly, I was pissed that he got married three months after I called off our engagement and also that he asked my brother to lie about it."

"Two years later, my brother was getting married, and my ex was the best man. I didn't care that he got married anymore, but it did hurt when he showed up with a 1-year-old and pregnant wife (since I can't have children, and he had said he didn't want them when we were together).

Later that night at the reception, I got really drunk and ended up talking to my ex's dad. Things escalated. We slept together, and I, being an a-hole who hadn't quite recovered from what his son did to me, continued to have a public relationship with his dad for six months."

—anonymous

4."It turns out my boyfriend was dating me, my sister, and my mom at the same time. When I was dating my boyfriend, I decided it would be best if he met my family before we got too serious. He met my siblings and parents but was the most fond of my younger sister and mother. I thought it was brotherly love until I visited my sister at college and found my boyfriend in her bed. They told me that they had been in a relationship ever since I introduced them and that, occasionally, they had a threesome with my mom. I was heartbroken and still haven’t forgiven my family. He and my sister are now married with three kids, and my mom is divorced."

—anonymous

5."I dated a girl for about nine months but was taking it slow as she was two years younger than me (I was 17). My older brother came to me and told me they had been sleeping together, and he had gotten her pregnant. It was okay, though. I didn’t love her anyway. Then he told me he didn’t love her either but was going to marry her because it was the right thing to do."

—anonymous

6."My sister-in-law dated one of my brothers not too far ahead of dating and eventually marrying my other brother. We live in a major metropolitan area, too, so it’s not like the dating pool is small. It’s been an ick factor that, for some reason, we’ve never really talked about it all. My family puts dysfunction to shame, though, so I can’t say I’m super surprised that this is just one component in all the other drama. But come on, it’s just gross."

—anonymous

7."I used to babysit for a lady who had four kids by a guy, then divorced him and married his FATHER...who she had another kid with. He was a long-distance trucker and gone all the time, so she started messin' around with the man from the other family I also babysat for, who had six kids! Yep, it was as ridiculous as it sounds. All men come from the same god."

—luckyangel30

8."A girl I was friends with as a child got involved with two brothers from a large family. She was in a relationship with one of them in middle school and got pregnant. After the baby was born, she started cheating with his brother. In high school, she got pregnant with his baby. All the drama came to a head one night and ended in one of the brothers stabbing the other. He was charged with attempted murder. I don't know what happened to any of them, but it makes me sad to think of those kids growing up in such a hostile environment, with children for parents."

—anonymous

9."My cousin ran away from home at 17, so her mom recruited her (the mom’s) boyfriend to help her search. Turns out, my cousin was hooking up with her mom’s boyfriend, and she was pregnant with his child. They now have three kids together and coparent just fine. The family has since forgiven everyone for the kids’ sake."

—anonymous

10."My stepdad is my biological uncle. My mum and my father divorced, and around the same time, my father’s brother was also going through a divorce. Because my father is a sociopath, my mum sought advice from my uncle because of their similar situation. A couple of years later, they started dating and then got married. It’s a bit awkward to explain to people, and there are always follow-up questions, but all that matters is my stepdad is the best dad I could’ve ever asked for, and everyone is so much happier and better off because my mum dated two members of the same family."

—anonymous

11."I’ve had the (un)fortune of dating the same women as my younger brother — at least six different women. The weird thing is? I never knew he had dated these gals previously, and each came after me when they had broken things off with my brother. The funniest (awkward) memory? One lovely gal and I were in the middle of a merry tryst when she looked me straight in the eyes and told me how much bigger and better I was at lovemaking than my brother! That’s how I found out about that one. I had a hell of a time keeping a straight face around my brother the next time I saw him. Years later, we had a good laugh."

—anonymous

12."A former friend took down a whole set of brothers. She dated the oldest one first. I was dating the youngest one, and he cheated on me with her. Then she moved on to the middle brother. She still cycles through them, even though the youngest is married to, you guessed it, one of her friends."

—bobi88

13."My brother's wife hooked up with one younger cousin, then an older cousin of ours, before meeting my brother at the same bar as she met my cousins."

—anonymous

14."This is about my ex-husband's current girlfriend. She was with his nephew first (my ex and his nephew are the same age due to huge gaps between him and his siblings). She claimed to have a baby by his nephew, who is a deadbeat. He never even raised the kid; his mom did. Four years into it, my ex's sister became suspicious that this kid looked nothing like her son. She got a DNA test done secretly, and it came back not his kid. His whole family cut her out due to it and didn't have anything to do with the kid."

"During this debacle, I'm married to my now-ex. She would call in the middle of the night asking him to come to fix her car and all sorts of weird shit. I became suspicious, but he denied, denied, denied. Years later, after our daughter was born, I found out he was cheating with her. I have no idea how long it had been going on. Now they have their own kid together, and his family has welcomed her back. I find it truly so gross and bizarre."

—applebeesgothgf

15."I dated one guy for about six months and then two years later hooked up with his identical twin brother…hehe."

—bcheese

16."My mom had a child with a childhood friend of hers. Their relationship never evolved past a 'friends with benefits' type of thing. They remained friends, though, and coparented well. Years later, he began a relationship with my mom's younger sister even though he was married at the time. He divorced, and they married and had children. My sibling has cousins who are also their siblings. Family gatherings were awkward after that. Elder family members despise the father. Those children are not accepted by other family members either. I have never told anyone about it because it feels like a Jerry Springer episode. It was an embarrassment then and now."

—anonymous

17."When I was younger, I dated two brothers. Now that sounds bad, but it wasn’t intentional! Guy A and I met in college and dated for four months. I never met any of his family, and we just weren’t meant for each other. Fast-forward a year, I started working part-time at a law firm and met Guy B. He was sweet and caring and everything I was looking for! We were together for about two months when he wanted to introduce me to his family. He invited me to his Mom’s birthday dinner, so I happily came along. When I got there, I was surprised to find my ex-boyfriend seated at the table!"

"We didn’t address head-on the fact we were together, but it got too weird for me, so I pulled Guy B to the side later into the night to tell him. He wasn’t upset but admitted it was weird for him. Eventually, we all talked about it and had a good laugh, but later, Guy B ended things because he couldn’t get past the uncomfortable thought of me being with his little brother. :/ AFTER that, Guy A and I got reacquainted and back together. We hid it from his family, knowing how they would think it was weird. We ended up eloping, and Guy B has yet to know. We’re worried it’ll be too weird for him. So, as far as he knows, we’re just friends."

—anonymous

18."I dated brothers seven years apart. Initially dated the first one in my early 20s, but ultimately, it didn’t work out. Got married and divorced to someone else. After my divorce, started dating again and started getting somewhat serious. Really looked at his family photos in his living room and asked about a specific person in the photo. It was his older brother from seven years before. Ended the relationship and didn’t tell either of them. Ran into the first one at a bar not long after, but didn’t talk to him."

—anonymous

19."Before I was born, my dad was married to my aunt and had three kids with her. Then he and my mom — her sister — did a midnight flit. My aunt didn't speak to my mom after that, but she sent a lot of hate letters. Here's the real twist: Later in life, when my mom got terminally ill, my aunt pretended to forgive and forget. She persuaded my mom to leave all her worldly goods just to my dad; then, when my mom died, my aunt got my dad to make a will naming her the sole beneficiary. Then he died a year later, leaving my aunt with everything!"

—anonymous

20."Yikes. My brother and his wife divorced 20 years ago but remained friends. They live on the opposite coast from me. Not long ago, my brother had a medical event that required a lengthy hospitalization. I flew out to help with decision-making and adapting his home for his new special needs. While I was there, me and the ex hooked up a couple of times. Then, after he was discharged from the hospital, they reconciled and moved back in together. I maintain that after 20 years, she was fair game, but still...awkward."

—anonymous

21."My best friend was dating a girl who had a twin sister when we were in high school. He cheated on her one night with her twin and got the twin pregnant. Their son is now 16 and is a really cool kid. My friend changed his ways and is an honorable man who owns up to his mistakes and takes pride in being a father."

—anonymous

22."A girl I did theater with dated brothers. She was a year younger than Brother 1 and three years younger than Brother 2. She dated Brother 1 on and off throughout high school and then started dating Brother 2 midway through college. And these brothers were very close and came from a very close-knit family! Also, I know for a fact that she slept with both of them and COMPARED THEM TO FRIENDS. It is weird."

—anonymous

23."I dated sisters consecutively. Would not recommend. Sister number one said it was cool, but it really wasn’t."

—melllvar

24."She was my uncle's long-term girlfriend for several years — we called her Auntie and thought they would eventually marry. Out of the blue, he ended things with her roughly a year before he passed away. A few months after he died, my other uncle was going through his brother's belongings and found some stuff that belonged to the ex-girlfriend, and phoned her up to return them. One thing led to another, and, as my mother (the sister to the two brothers) put it, 'they connected in their grief.' Christmas that year was awkward AF let me tell you."

—anonymous

Did you or someone you know date two members of the same family? Let us know in the comments below or via this anonymous form!

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