Dating

9 Guys Who Dated Their Best Friend’s Ex Share Exactly How That Went

There’s absolutely nothing messier than dating one of your friend’s ex-girlfriends. If he broke up with her, he’ll probably wonder why his friend is dating someone he had some serious problems with. If she broke up with him, it’s even worse. He’ll wonder how his friend could get together with someone who broke his heart. Could a friendship even survive this? I wanted to find out, so I asked 9 guys who dated their friends’ exes how it went. Responses have been lightly edited for readability.

  1. “I actually liked her before my friend did. I had literally been crushing on her for months before my friend ‘Mike’ swooped in and invited her to some stupid dorm event. They started dating not long after and I never really got over her. After he broke up with her, I decided to take my chance before someone else got involved. We casually went out for ice cream and things started going really quickly. I think she saw me as a good rebound? Word eventually got back to Mike and he didn’t talk to me for the rest of the year even though we lived in the same dorm hall. The relationship didn’t last, but I still don’t regret it.” — Chad, 24
  2. “My story isn’t very dramatic, but I guess I can still share it. My best friend in college was two years older than me and had been dating this girl Katie. He graduated and decided to take a job with Amazon in Seattle. This is pretty far from where we all went to college, so he decides to break up with Katie. The summer after he left, I start hanging out with Katie a lot—we were friends while she was dating my friend. One night we were just hanging at my apartment and one thing led to another and she stayed the night with me. I messaged my friend a few days later mentioning that I was ‘interested’ in Katie and he told me to go for it. Katie and I never really dated, but it was a really fun summer.” — Omar, 29
  3. “I wouldn’t actually call him a ‘friend’ but one of my fellow brothers in my fraternity had just broken up with his girlfriend for some stupid reason and I decided to reach out and see how she was doing. She had hung out at the house a ton and basically become ‘one of the guys.’ To be honest, I probably liked her more than my actual fraternity brother. Anyway, after I reached out to her, we decided to get lunch. She was pretty torn up about the breakup and we became really close friends pretty quickly. A few months down the line, that led to us dating. When my fraternity brother found out, he blew up at me in front of our entire house. He really came off as completely unhinged. Pretty much everyone sided with me because it had been like four months since they broke up and he trash talked her all the time. We are still dating two years later, so definitely no regrets.” — Alex, 26
  4. “Uh, it did not go well at all, I’ll start with that. My first true friend in college was dating this girl Anastasia who he had been dating since sophomore year of high school. They were always fighting all the time and it was obvious that it just wasn’t working out. Eventually, she broke up with him. She lived on the other side of campus, but I guess since we were really the only people she knew, she kept hanging out in our residence hall. One night we were up late studying after everyone else had gone to bed. Before I knew it, some light cuddling turned into a full-blown make-out session. If you haven’t guessed already, in walked Anastasia’s ex-boyfriend aka my good friend. We tried to break apart when the door opened, but the damage was already done. He didn’t say anything at the moment, but he sent me a gigantic text message that night and our friendship was beyond over. I don’t know if I regret it or not. I probably should’ve been smarter about making out in the common room of our shared dorm room, but it was college.” — Joshua, 27
  5. “Part of the problem was that I actually started seeing my best friend’s ex before she was his ex. I was 16, stupid, and with absolutely no concept of what friendship was. When my friend found out, he was unsurprisingly pissed. We didn’t talk for a year but eventually became close again and I was actually recently the best man in his wedding.” — Cory, 22
  6. “To make a VERY long story short, my best friend and this girl were in a constant ‘on again/off again’ pattern of dating. He could never make up his mind between wanting to keep her or being a free bird player on dating apps. During one of their ‘off again’ periods, me and her hooked up at a party and saw each other casually for a while. We usually stopped meeting up when she and my friend were ‘on again,’ but sometimes we didn’t. I don’t think he ever found out, though they’re engaged now?? I’d bet money that wedding never happens.” — Mohammed, 25
  7. “My best friend hadn’t exactly ‘dated’ this girl, but they had gone on a few dates. As it turns out, she really didn’t feel any chemistry and asked if they could just be friends. That’s (for better or for worse) where I come in. I asked if she wanted to go to the winter zoo lights at our local zoo and she said yes. We had a great time and decided to go out again, and again, and again, until it was super obvious we were ‘a thing’. I tried to talk to my friend about it, but he told me that he already knew and was pissed. It didn’t end our friendship but definitely put a strain on it until we stopped seeing each other about a year later.” — Arnie, 23
  8. “My buddy ditched this girl for being ‘too clingy’ because she texted him every once in a while. I thought she seemed great, so I asked her out on a date and things really clicked. We kept seeing each other, and when my buddy found out he kept giving me a hard time about it. ‘Cody really likes clingy girls!’ and saying shit like that. I eventually told him to shut the hell up and he did. The girl and I are now engaged to be married, so I think I won?” — Cody, 32
  9. “I was pretty shy in college and wasn’t good at meeting girls. The only girls I knew were really the ones in my friend group, and all of them were dating except for Nichole who had just broken up with another guy in my friend group. I started flirting with her hardcore and we went on a few dates. When her ex found out, he pretty much trashed me to the whole friend group and things were really tense for a while. I wish I had just tried to find a girl on a dating app instead of starting all that drama.” — Sean, 21