20 People Share Their Worst Break-Up Stories, And Oh Boy, Do People Have Issues

Relationships are hard. Breakups are hard. It’s the natural course of things. Sometimes, you just have to do it and there’s no easy option. And BOY breakups do not always go smoothly (do they… ever?). With that many feelings flying around, it’s pretty inevitable that people are going to slip up.

man and woman holding each other's hands
Photo byAndrik Langfield on Unsplash

This online community recently shared some other WORST stories.

1. Moody

“We had an argument a couple of hours before about something I can’t even remember, and he texted me saying, ‘Are you done being moody now?’ So, I sent him the YouTube link to Taylor Swift’s ‘We Are Never Ever Getting Back Together!’ I never ever got a text back. 😂”

 tanzilaasghar

2. I hate this person

“I gave them a Band-Aid and told them they would need it because they were cut.”

 anonymous

3. Not serious enough

“He uninvited me from his 21st birthday party the day before but asked me to come over before the party to do cake and gifts with just him. Apparently, eight months wasn’t serious enough for me to meet a bunch of his friends, and it was not an all-guys party. I went over the next morning during the time he set aside, but instead of gifts and cake, I handed him all his stuff and wished him a happy birthday.”

 sschulzaib

4. Oh.

“When I was in college, I’d been seeing a guy from another class for about a week and realized that there was just nothing there. One day, I was walking down the stairs from the auditorium with classmates, and one of them said, ‘So, when are you ditching Neil?’ Then, who steps out from the shadows under the stairs? Neil. ‘This isn’t quite how I pictured this,’ I said awkwardly; he just said, ‘Oh’ and left.”

 retrocrebbon

5. Long distance

“We were long distance (about a 2-hour drive apart) and dated just under two years. We hadn’t seen much of each other, and I realized we wanted different things (I was a single mom with a 3-year-old and wanted to get married…he did not seem interested). Valentine’s Day was approaching, and I told him I didn’t think we should spend the day together since things had seemed ‘off’ with us recently. He took that as an ‘Oh, I should go to town and surprise her even though she said not to!’ He knocked on my door while my son was taking a nap, and I was so angry he showed up that I broke up with him right there. I went up to his house the next week to pick up my things, and he greeted me in a bathrobe, completely naked underneath, thinking I’d have sex with him and everything would be fine.

“The kicker…he wouldn’t move to be with me while we were together. But, for the last few years, he’s lived a mile from my dad, and I have to drive past his house to get to my parents!”

 kelsey33

6. Oops?

“I was dating someone when I started college. Obviously, it did not last. However, I kept up the relationship the first semester of my freshman year and convinced his family not to go to a restaurant for Thanksgiving. I assured them I would cook the entire meal in their kitchen. I’VE NEVER COOKED A DAY IN MY LIFE! Two days before Thanksgiving, I texted him and told him we should end things. I have no idea what his family ended up doing for Thanksgiving!”

 anonymous

7. Disney Breakups

“During our anniversary trip, my ex and I went to Disney World. We were already arguing leading up to it (we were long-distance), so we were on the brink of breaking up. We were doing well that day (only argued once) until we were in line for a ride, and a random guy messages my IG, saying, ‘Text me at this number,’ making it seem like I was talking to him (which I wasn’t). My ex saw it and was pissed, so I tried calming him down since we were next to go on the ride. We got on the ride, and he kept his arms folded the whole time. I decided to enjoy the ride with the family sitting across from us. Long story short, we walked around the rest of the park not speaking and finally broke up that night right after we saw Tinker Bell cross the Disney Castle. I broke it off with him because his insecurities (and the fact that he ruined the trip) were too much. It was an awkward walk back to the park entrance after breaking up.”

 anonymous

8. Powerpoint

“I put a flash drive in his mailbox that had a PowerPoint presentation of why things weren’t working out on it.”

 kroxdz

9. She moved on

“I broke up with my ex of five years over an audio-only Skype call. She had her video on; I kept mine off. She had been starting to look at wedding venues and rings, and I just panicked. I told her I didn’t see a future with her. Stupidest mistake of my life. She moved on to a mutual friend of ours, and they’re expecting their first kid after six years together.”

anonymous

10. Stayed the night

“I wanted to break up with my boyfriend for a long time. He had been unemployed for almost a year and seemed generally unmotivated. I went to a wedding with him as his +1. It was over two hours away! We stayed the night there, and he drove me back to my place. I broke up with him not 10 minutes after we’d arrived. I felt bad for doing it right then, but as I wanted to do it in person, I’d either have to do it right after I was his wedding date or schedule a date only to break up with him. I wanted my time back, so I chose the former. My consolation about this is he knew it would be coming.”

 anonymous

11. Ice skating

“I didn’t necessarily break up with him, but I think I initiated it. For context, I’m a lesbian. I was figuring this out at the time. I lost feelings for him and wanted to let him down easily. My way of doing this was telling him, ‘I’m gay, but I still like you’ (I didn’t). After, we went ice skating. Soooo. Awkward.”

 anonymous

12. Email

“After almost a year of dating, I had enough of his crap. So, I dumped him via email. His work email.”

 anewfan2018

13. Whoops

“My way was not awful per se. At least it wasn’t in the beginning. I was dating him for a couple of months and realized that I wasn’t over my ex, so I decided to break up with him in a nice way. You know, I would say it’s not working, and that’s it. We met, and I started the sentence with the name of my ex instead of his actual name. I did not need to say another word.”

 anonymous

14. A note

“My high school boyfriend of two years broke up with me by putting a note in my shoe for me to find. Context: I was in marching band all four years of high school. It was a tradition every year before semi-state and state that we would dress up really fancy for school the Friday before the competition. So, there I was the day before semi-state, all dressed up and walking to the band hallway after school to change for practice. I had a lot to carry, and like the previous years, he helped me out by carrying my tennis shoes. When I went to put on my tennis shoes, I found a breakup note that he had put inside one of them. Being a calm and collected 17-year-old, I dipped out on band practice and set up a hammock in the middle of my house, and swung there ’til my parents dragged me to a gun range that night.

“The next guy was a year behind me in school, and while I was away for the military, he asked if he could go to a dance with a girl. I was like, ‘Of course, enjoy your high school experience,’ and he said: ‘Well, what if she comes back to my place and ‘stuff’ happens.’ So, I told him he should find out because we weren’t dating anymore. Then, I made it very clear I was breaking up with him over PLANNED CHEATING. Not all bad, though. My friend group had plans to get ice cream that day, and everyone bailed except the boy I married six months later. Seven years down the road, we are happily married 26-year-olds with six fur babies! <3”

anonymous

15. Tragic!

“This is a tragic classic: over text. I was young and didn’t know how to assertively and maturely communicate that I wanted to end the relationship. So, brace yourselves. He and I had a phone call, and the disconnect between us was clear as eggs on a plate. After he and I hung up, he texted me, saying that we had the choice to either move in together or break up. I responded that I wanted a break. He texted back with an ‘If you say you want a break again, we’re done.’ I texted back, ‘I want a break,’ to which he responded with ‘GOODBYE.'”

anonymous

16. Happy anniversary ?

“I never bought him a Valentine’s Day gift in grade seven. … I never spoke to him again. Mohammed, if you’re out there, happy ninth anniversary.”

anonymous

17. Ghosted

“I ghosted him on a trip while literally always being [around] him. It was a competition of sorts. We went with other friends, but I wanted to break up for some time and was worried that would affect his performance at the competition (which meant a lot to him). So, I said to myself I would break up with him afterward. While in another country, young and with friends, I wanted to have fun with them, not him, so I pretended he didn’t exist. I was always in the opposite part of the room, avoiding sitting next to him, being in the same car, etc. He was confused but did well in the competition. He won some awards. When we came back, it was the finals, so I postponed the breakup again and ghosted him with the excuse of studying.

“During summer break, I missed that deadline, too. So, basically, I wanted to end the relationship in April and then just waited for him to do that for me, but the poor soul didn’t. September came, and I finally did it (after not contacting him for three months). I’m the worst!”

anonymous

18. Well. Ouch.

“I broke up with my boyfriend on Valentine’s Day, which was, unfortunately, also his birthday. 😬”

anonymous

19. Changed schools

“This was when I was in high school. (Mobile phones were not so common back then.) I attended a school out of my hometown and stayed in a dorm. I had a boyfriend for a little bit over a year. A little background info: This town that the school was in was small, and while you were preparing for college, you had to leave the town during weekends to attend courses, stay in different dorms, etc. It wasn’t an ideal way to prepare for a college exam. So, I decided to change schools and move to a different and bigger city during the summer break of junior year. I CHANGED SCHOOLS WITHOUT LETTING ANYONE KNOW. I just never went back. I didn’t tell my boyfriend that I changed schools, and it was the end for us. He had to learn from other people later on that I changed schools and was never coming back. I really liked him back in the day, though. He was super cute, too. Have no idea why I did that.”

anonymous

20. What an ASSHOLE

“I let her walk in on me in bed with another woman. The other woman was a willing participant. I had a chance to apologize 20 years later, but that apology happened 20 years ago, and I still think about how awful I was to do that.”

anonymous

Jason Mustian

Jason is a Webby winning, Short-Award losing humor writer and businessman. He lives in Texas with his amazing wife and four sometimes amazing kids. All opinions are mine and very dumb.