11 People Share Their Weirdest, Most Awkward ‘Sex With Ex’ Stories

1. “We were both invited to MY friend’s wedding (she was my friend first), and I was totally fine with both of us being on the guest list because my ex and I agreed we could both be mature about it. He texted me the entire wedding saying how good I looked, and how he wish he came there with me instead of his plus one. Long story short, he told me to meet him at the elevator when dinner was being served, took me into the men’s room and went down on me for a solid 20 minutes. I missed the salad course, but I’ll have oral over salad any day.” Kristin, 27

2. “We found each other on Tinder. We both swiped right, never messaged each other. The weekend rolls around and he messages me (on the app) at 2 am saying U up? I said yeah, come over. He did, and I think you know what happens next. TLDR: I rekindled the flame by swiping right on Tinder and answering his booty call.” Hailey, 25

3. “My ex has a five year-old daughter, who was really hard to say goodbye to when we broke up. My niece is seven, and my sister let me take her to a local carnival, this was about 4 months after the break up. Of course, we ran into my ex and her daughter, and it immediately made me miss both of them. I called her later that night, and she said, ‘Caylin’s sleeping if you want to come over.’ (Caylin is her daughter) I was at her house within the next half hour.” Ricky, 27

4. “I ran into my exes mom at the grocery store. She asked me how I was, and told me she missed me, and that I should give her daughter a call some time. I texted my ex that day to let her know what her mom said. Pretty sure she was humiliated, but continued to text me regardless. We met up that weekend, and when I was in her bed she said, ‘Thanks, Mom,’” Greg, 26

5. “My ex is the brother of my sister’s best friend, which is a little awkward because he totally screwed me over and my sister’s friend was super embarrassed about the whole thing because she set us up. I went snowboarding one weekend with my sister and her friend, and of course my ex texted me saying he heard I was with his sister, which then caused him to apologize for everything he did to me, bla bla bla. I was single AF at the time, and he was being sad and desperate, and basically asked if I would ever give him another chance. I told him if he drove up to the mountains, I might think about it. He showed up to the house we were staying at, we fucked, and I legit never talked to him again. How’s it feel asshole?” Lisa, 26

6. “Technically it wasn’t sex with my ex, but I fucked his twin brother. If that’s not revenge I don’t know what is, and yes I know I have no soul, and will probably end up alone forever.” Macy, 24

7. “My ex and I managed to stay somewhat friendly, and I had no one to dog sit one weekend when I was going away. As a last resort I went on a limb and asked if he would, I even offered to pay him. He agreed to which was super nice of him. When I came back on Sunday to pick up the dog he didn’t charge me, but I gave him a tip that I think he thought was well worth it.” Christiana, 26

8. “My cousin set me up with one of his friends from college. It obviously didn’t work out, and I don’t hang with my cousin all that often so it wasn’t like I had to see him everyday. My cousin had a Superbowl party this year, and I knew my ex would be there. Everyone was watching the game upstairs in the living room, and I went downstairs in the basement to bring up another case of beer. While I’m getting it, my ex comes down and asks if I need help. He started helping me and making small talk, and before I know it we’re fucking on my cousins treadmill. I had some major burns on my ass, and didn’t even cum, so not worth it.” Lauren, 25

9. “My ex and I have a lot of the same friends, which is tense, but we make it work. We all took an awesome group vacation to Miami, my ex included, and one night we went to an enormous dance club and decided to take some Molly while there. So we were both rolling and couldn’t keep our hands (or lips off of each other), and while we were on the dance floor we both started dancing with this girl who had rainbow dreads, and we kept touching them basically mesmerized, and we decided to give her some Molly too. We ended up bringing her back to the hotel to have a three-some. To this day we still don’t know her name, we just call her Rainbow dreads girl. It was an interesting vacation.” Jessie, 26

10. “My friends and I made a bet on some stupid trivia fact that I INSISTED I was right about. I was so sure that I was right, that when they bet me if I was wrong I would have to text my ex and ask her out, I agreed. Turns out I was wrong, and my relentless friends forced me to text my ex asking if she’d go to dinner with me. To my surprise she actually answered and said she’d be willing to. I was already enough of an asshole with the whole bet thing, so I decided the least I could do was show up. The whole time she tried talking about what went wrong with our relationship, and got all emotional throughout the entire dinner. When I drove her home she started crying. Basically the only way I knew how to make her stop crying was to kiss her. So I did, and then she started getting way into it, and we had sex in the back seat. The sex was good, but the situation was just way too fucking weird. TLDR: I always think I’m right, which lead me to lose a bet that involved fucking my ex.” Harry, 26

11. “My ex left one of her bras here after we had broken up, and she said she wanted it back. I told her I wasn’t going to hand deliver a bra and that if she wanted it she could come by and get it. She comes over, I answer the door, and she asks for her bra, but before doing so she decides to tell me she isn’t currently wearing one. I was super confused/turned on and didn’t know what exactly she was suggesting. All of the sudden she’s taking her shirt off and we’re making out. After we were done, she walks out the door and what do I see on the ground next to my bed? Her fucking bra. It’s still here. Definitely her strategy to come back here and fuck me.” Justin, 25

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