17 "Running Into An Ex" Stories That Are So Awkward It Hurts
"My ex checked me and my new husband into our hotel room on our wedding night."
1. "I had just gotten out of wisdom tooth surgery and ran into my ex in the waiting room. I was not over him, and, still looped up on drugs, starting crying and saying, 'I love you!' My mom had to drag me out of there."
2. "On my wedding night my husband and I, still clad in a wedding dress and tux, went to check in at a fancy hotel. Turned out the guy behind the counter was someone I dated in college. So yeah, my ex checked me and my new husband into our hotel room on our wedding night."
3. "I was fooling around with a guy once when he thought it'd be a good idea to invite over one of his friends for a threesome. The friend turned out to be my ex."
4. "After tearing my ACL and having surgery, I started physical therapy. At one session, I noticed someone on the bike next to me who also had an ACL injury. I looked closer and saw it was my ex (who I had not seen or spoken to since our rough breakup). Let’s just say PT was quite awkward the next few months."
5. "I got randomly assigned a college roommate who turned out to be my ex’s new girlfriend."
6. "I walked off an 11-hour flight and the first person I saw was my ex. He was with his parents whom I had never met but heard so much about. They were there waiting for his new girlfriend who was on my same flight."
7. "My new husband and I went to a burlesque show for our first married Valentine's Day and were shocked when they announced the first burlesque dancer — because it was my husband’s ex-girlfriend. So we spent our first married Valentine’s Day watching my husband’s ex take off her clothes for the crowd. Awkward."
8. "My pregnant coworker went home to the small town she grew up in for a visit and her water broke. The only medical provider available/qualified to sit and stare between her legs for the nine hours of labor? Her high school boyfriend."
9. "An ex came into my workplace with their new girlfriend after I'd injured my face and had this huge Band-Aid on my chin and scratches everywhere. I got introduced to the new girlfriend like that — it definitely wasn't the 'look what you lost' moment I wanted."
10. "My ex is in my class and we had been avoiding each other for a few months when the teacher randomly assigned us to be partners on a project. We had to FaceTime, text, and go to each other's house to work on the project. It was so awkward."
11. "I got a job and on my first day I walked in to find my ex was working there as well. We avoided each other until one day I got a text from him saying, 'Don’t worry, I’ll quit.' Haven’t seen him since!"
12. "I was in line at the dollar store with my new boyfriend when I looked outside the store and saw my ex-boyfriend staring at me. He started giving me the middle finger so I responded with my middle finger. Everyone in line, including my new boyfriend, looked at me like I was insane."
13. "I bumped into my ex in a shop while I was buying tampons. I panicked and said, 'Well, at least I’m not pregnant!' and ran away."
14. "My ex-husband cheated and left me with a newborn and toddler. Several months later, after having been up all night with a sick toddler and colicky infant, I dragged myself to Starbucks for a much-needed coffee. Who do I run into but my ex and his new girlfriend. Worst. Morning. Ever."
15. "I was working for orientation at my university. Due to my position, I was the only student working with transfer students. Well, my ex transferred to my school and I had to spend eight hours guiding him around campus. Within two weeks he withdrew from the university."
16. "My ex used to always drive me to work. After we broke up, I would take the bus to work. One day, as I was waiting at the bus stop, his car pulled up directly in front of me and stopped at the light. We both had to awkwardly look around to avoid eye contact for what felt like the longest red light ever."
17. "On New Year's Eve I ran into my ex and his date at a big, fancy party. I tried to get away from them before they saw me, but tripped over my feet and ended up sprawled out on the ground with my Spanx showing. He had to awkwardly help me off the ground."
Submissions have been edited for length and/or clarity.