Nobody likes breaking up with their significant other. It’s an uncomfortable experience for everyone involved, and there’s no “right” way to do it—it’s not like there’s a handbook for those sorts of situations.
Sometimes, breakups are awkward, ridiculous, and downright embarrassing. The silver lining: Bad breakups make for great stories. In several threads, Reddit users shared the stories of their weirdest breakups. We collected a few of the best examples, then edited them slightly for grammar and readability.
When your boyfriend dyes his hair to look like a predatory cat, that’s a red flag.
“I was dating this guy in high school, and he dyed his hair cheetah-print,” wrote one Reddit user, whose account has since been deleted. “Something about that dye job changed him. Not over time—instantly.”
Well, in his defense, cheetahs do everything pretty quickly.
“He went from being a normal guy to ‘I am too alternative for words,’ and I wanted no part of it. At lunch, I had to sit him down and have a talk with him about it. I told him that he was kind of acting like a [jerk], and maybe he was letting this new look get to his head.”
“He took my hand and said I needed to accept him for the new person he was, which I guess was a cheetah or something, so I told him I had to set him free. He looked at me with these knowing eyes, and that ended the most awkward four-day relationship I have ever had.”
Oddly enough, that’s not the only hair-related breakup story we found.
“I dated a girl in high school who was an ‘actress,’” wrote schellinky. “One day she came to school with her hair in cornrows—for one of her plays, but I had no idea—and it was also dyed purple or pink. I can’t remember.”
“When I sat down with her at lunch, she asked me, in front of all of her friends, if I thought she looked beautiful. I said, ‘In all honesty, I preferred your older hairstyle.’ She then proceeded to call me shallow (in front of all her friends) and broke up with me. I didn’t even argue, I just walked away. What did she expect me to say?”
Communication is crucial in any relationship.
“Once, a woman broke up with me over a very weird conversation…that simply had not ever occurred,” wrote Mmedical. “She was making references to it. The conversation was apparently over the telephone—I had called her at work.”
“I was dumbfounded. I told her that I didn’t remember any of this—that I did not even speak with her that day. She refused to believe me and broke up anyway.”
“Just to be certain I wasn’t capable of completely forgetting an entire conversation, a couple weeks later, I checked my phone bill (since her work was long distance, it would have been itemized). There was no call to her work number on the day she said it happened, nor were there any calls to her work in the prior three days.”
“Maybe she dreamed it? Maybe someone called posing as me? No, I did not pursue it any further. Leave crazy alone.”
Sometimes, bad situations can take care of themselves.
“I started going out with a girl in my first year of university who, at some point after the initial happy period, became absolutely insane,” wrote SausagePlease. “She was breaking up with me pretty much every day, public screaming at me, etc.”
“So I told her that if she broke up with me again, then that would be it for good. She doesn’t do it for a few weeks, at which point I’m thinking, ‘Actually, I don’t really want to be with this girl.’”
“Eventually, she goes crazy at me again and says, ‘That’s it! You’re dumped!’ She realizes what she’s said and goes white as a sheet. As she starts saying, ‘I didn’t mean to say it,’ I just went, ‘Oh, sorry, no backsies!’ and left.”
When someone doesn’t have the nerve to break up with you, things can get…awkward.
“I was engaged and went away for the summer to work at a school in Central America,” wrote sdwescott. “The whole time, I tried to call my fiancé, but we only connected a few times.”
“On the day I returned, I had a layover in Houston on my way back to Portland. While sitting at my terminal, I was paged over the intercom to pick up the nearest white courtesy phone. I ambled over and was connected. It was my fiancé paging me, at the airport, to tell me he couldn’t pick me up in Portland because he’d fallen in love with another woman.”
“That happened. Our airport breakup was the last time I spoke to him.”
Breaking up is hard to do…especially when you’re a kid.
“This occurred during my junior high years; just [picture] early, awkward preteens,” wrote PYRoBU. “I’m riding the bus home with my ‘girlfriend.’ We’re awkwardly holding hands, and then her stop comes up.”
“She looks at me, grabs my other hand, kisses my cheek, and says, ‘You are a cage, and I’m a bird. This is over.’ And then she walks away, and that was the last time I conversed with her.”
At least there was an actual conversation. That’s not the case with this next story, courtesy of LognessMonster:
“A friend of mine in middle school was broken up with by his girlfriend in this poem: Roses are red, violets are blue, garbage is dumped, and so are you.”
When you’re going through a breakup, try not to project your feelings onto others.
“I was in communications class in school,” wrote le_ironic_username. “It was a class where we’d learn pointless [stuff] like how to write reports and such using Microsoft Word.”
“Anyway, the computers had remote monitoring stuff on them that permitted teachers to spy on your screen, lock the keyboard and mouse, and project your screen onto the overhead projector for all the world to see. I was aware of this, but I always risked checking my emails anyway.”
“One fine morning, I go to check my emails. I see one from the girlfriend (at the time).”
“So I click on it and start reading. I am just reading the last few lines, in shock, processing what I have just read—it was the break-up email. She knew I checked my emails and thought it was less awful than a text or phone call—when the mouse stops working.”
“I see the projector blink into life, displaying the Hewlett Packard logo. That sadistic [jerk] of a teacher is obviously about to que up my heartbreak for all to see. I have mere seconds.”
“I did the only logical thing: I violently ripped the power and network cables from the back of my desktop and left.”
Some people simply don’t get the message.
That’s forgivable if you don’t actually send them a message.
“We’d only been dating for a few months, but things seemed like they were going great,” wrote mattpelaggi. “There were legitimately no signs of trouble. I call her one night before bed, as we did, and she just didn’t answer. I figured maybe she was asleep or something, so I texted her the next day. No response.”
“I waited a few days, then sent her a message asking what was up. She respond with this gem: ‘I just felt like I wasn’t being listened to by people in my life, and it got to the point where I wanted to just get away. Explaining myself wasn’t working, and the pressure didn’t subside, so I stepped away. I’m sorry it involved you, too. I don’t hate you or anything, I just needed to feel better. Sorry for being selfish, take care.’”
Remember, folks, if you don’t communicate with your partner, you can’t expect them to know how you’re feeling. That’s also true for the end of the relationship—if you’re ending things, make sure that your feelings are crystal clear.
“After several months of dating, I told this guy that I didn’t want to see him anymore,” wrote lookylou. “But I guess I wasn’t firm enough, because I came home from work several days later on Valentine’s Day to find him waiting for me.”
“It was a small town, and I didn’t bother locking my doors. He had scattered rose petals all over, had cooked dinner and drawn a bath, scattered with more rose petals. There were rose petals on the bed along with gifts—including handcuffs and a blindfold.”
That’s a little creepy.
“He was harmless, and still is,” they wrote. “He just really didn’t get that I had broken up with him. I led him out to the front porch where I spelled it out quite clearly. Then I started locking my doors.”
All things considered, this breakup went pretty well.
“I had my first boyfriend ever [during] my freshman year in college,” wrote sassymcmittens. “On summer break, he didn’t like that he couldn’t spend the night with me [with] my parents around. I’m in my room one evening, and it occurs to me that I haven’t heard from him in a couple of weeks.”
“Not at all upset, I call him up and ask him if we’ve broken up. He stutters and says yes. I say, ‘Okay, leave my stuff in the mailbox.’ He stuttered ‘Yes,’ and did as I asked a week later. I never even missed him.”
That’s exactly what we’d expect from a first-time relationship. This next story, however, is a little more immature.
“My boyfriend started a fight with me over a piece of pizza that was given to me by my roommate,” wrote casual_penguin. “He said, ‘I didn’t want it to be your pizza, I wanted it to be our pizza.’ He was 24. I was 20 with a low-bulls*** tolerance, so I said [forget] it.”
That’s pretty unbelievable, but we’d have to know more about the pizza to say whether or not the guy’s actions were totally unwarranted.
The phrase “pining for someone” isn’t supposed to be taken literally.
“I dated a guy for a few months before discovering he was totally cray-cray,” wrote smokingcupcake. “He didn’t tell me until after three months that he had a son, but, according to him, his ex was a fairly famous model. The only proof he had was one of those generic wallet pictures.”
That sounds totally legitimate to us.
“He did, however, have pictures of his son and his family to let me know that he really did have a kid. Why no one said anything to me upfront, I have no clue. He started showing me this random picture all the time, talking about how great his ex was, etc.”
“I finally decided to break up with him because I developed feelings for a mutual friend. A group of us used to hang out all the time, the other guy admitted his feelings for me, and I decided to end things with the other guy. By this point, [my ex] would call me in the middle of the night to either talk about his ex, try to convince me to go hunting with him, or ask me if I wanted to help him raise his son. Oh—or he would call to see if I wanted to get married and have kids with him.”
“I decide to break up with him when we were literally sitting in the middle of Denny’s. I believe it was when he once again pulled out the wallet picture. He throws a massive fit in the middle of the place, runs outside, and proceeds to start kicking a tree. This leads to him full-on fighting with a tree, complete with fake karate moves. I try to talk to him, and he tells me to leave before he ‘hurts’ me.”
Again, this guy sounds completely normal and totally healthy. We’re not seeing what the big deal is.
“A few weeks later, I’m back at the same restaurant (stupid, I know) and I see him. He acts perfectly calm, seeing as how he’s on a date with another girl. He leaves with her and comes back a few minutes later by himself. He goes back into the parking lot and starts fighting with the same tree once again.”
“We take this as our cue to leave, but nope, he doesn’t want that. He starts screaming and crying, all while still attacking this random tree. We end up having to call some of our mutual friends to come and take him home.”
“I actually ended up dating the mutual friend for several months. One day, we decide to go Christmas shopping together, so we both met up after work. He gives me a kiss when we’re done, we make plans to meet at a restaurant nearby for dinner, and we go our separate ways.”
“I never see him again! He literally just got in his car, went home, and planned to never talk to me again. I later found out that the ex told him some horrible things about me and he decided that he didn’t want to be a part of my craziness. Yup, attacking a tree is totally normal, but the girl who broke up with someone who would attack a tree is crazy.”
Sometimes, you can’t stomach your partner’s bad behavior.
“I was dating a girl who was a vegan for about two months,” Troll_Logic wrote. “We went to a birthday dinner for a mutual friend of ours. I’m not a vegan, so I went ahead and ordered a 16-ounce steak.”
You can probably see where this is going.
“My ex stared at me like I was crazy, but I didn’t think anything of it. It wasn’t until I was about halfway through eating my steak that she blew up on me. She went on a rant how she couldn’t believe I could eat that, and how bad it was, blah blah blah. I broke up with her the next day.”
Granted, we don’t know what else was happening in the relationship, but if you’re so horrified by your significant other’s diet that you make a scene in public, it’s probably a good time to step back and reassess things.
Of all of the terrible breakups we read, this one’s our favorite.
Maybe “favorite” isn’t the right word, but if you’re looking to experience some secondhand embarrassment, this story definitely delivers.
“My girlfriend of a year broke up with me by sending a video of herself singing a breakup song that she wrote,” beingDevisor wrote. “It included a background dancer—one of my good friends.”
“I was at a party at the time she sent it, and I foolishly played it aloud so all my good pals could hear it (and hear my heart break). Definitely the worst.”
And yes, beingDevisor shared the video. We’ll warn you—it’s not very good, but hey, you’re not pressing play for its musical merit, are you?