Most breakups are really tough, regardless of the circumstances. But some stories just really take the cake in the most awkward/horrible/worst breakup category.
1. The stick figure artist:
My boyfriend met me at Wagamama for lunch, and while we were waiting for our orders, I noticed him scribbling something on a napkin. He sometimes scribbled me funny/cute notes. With a shy smile, he slid the napkin across the table to me. I smiled back until I realized that the note read: "I really love you, but not that much. Can we be friends with benefits??" And next to the writing was a sketch of a stick figure with an erection, standing next to a smiling stick figure with boobs.
Before I could react, he mumbled, "Be right back," and walked out of the restaurant with his corduroy jacket still on his seat. It took me around 40 minutes to realize he wasn't coming back. About four days later, he texted saying, "I'm horny. Can I come over?" Followed by, "Too soon?" Needless to say, I blocked his number."
—Cat Alle, Facebook
2. The divorce-by-text:
After being married for four years, I got a text message from my ex saying, "I think we rushed into things." Oh, OKAY. Thanks for letting me know now?!
3. Roadkill and flowers:
My sister was on the verge of getting married to this guy, when she found out that he’d had another fiancé in a neighboring country during the entire two years they were together. When my sister ended things, he pleaded with her to reconsider, telling her that she was the only one he loved.
After she refused and turned him away, dead birds started popping up on our doorstep every day for two weeks. These weren’t taxidermy birds. They were roadkill birds. The sick part was he also sent her flowers at the office every day for two weeks, as well.
4. The good deed, gone wrong:
For background, this happened when I was in 12th grade and in a two-year relationship. My boyfriend's mother was dying, so he wanted to go back to Indiana to be with his family. He was super close to her so I encouraged him to go be with her and transfer to a community college near her so they could spend her final few months together. While there, he apparently got a waitress pregnant, and married her on my birthday. He didn't even tell me, his best friend did.
—Samantha Ryan, Facebook
5. We are never, ever, getting back together:
My ex-girlfriend and I️ dated for two years, and lived together for a little over one. She broke up with me and kicked me out of my home, all while blasting "We Are Never Ever Getting Back Together" by Taylor Swift, and sending me text messages from the upstairs bedroom that I️ needed to leave. The kicker: We had a pet hedgehog together, that at the time, was perfectly healthy. After not speaking for two weeks, she called me up to tell me that he was dead and that I️ needed to take care of the body and cage because he had been rotting in her room for an entire weekend. Worst. Breakup. Ever.
6. See you never:
After three years together, he, out of nowhere, changed his relationship status to single on Facebook and moved out of state. The only reason I found out was because I logged into Facebook and saw his status changes. I never ended up hearing from him besides his best friend sending me a message a few days later that said, "Oh, he says he's sorry."
—Seth Traver, Facebook
7. The haircut conundrum:
I used to have hair halfway down my back. But about three years ago, I asked my ex-boyfriend if he'd still like me if I had a bob. And after he said yes, I decided to do it. I guess he didn't think it'd actually happen, because about two days later he broke up with me since I apparently ~looked like a boy~ now. It just so happened to be on Valentine's Day, too. What a dick.
8. The unwarranted birthday surprise:
It was 12:30 a.m., which meant it was 30 minutes into my birthday. My then boyfriend, aka the man-I-thought-I️-was-going-to-marry, was asleep next to me. So l looked at his phone to see if he was planning a surprise for me. I'm horrible about wanting to find out plans/surprises. So I searched my name in his texts (we never hid our phones from each other or had passcodes) and proceeded to discover that he had cheated on me three months earlier and the girl was coming into town next weekend! Happy birthday to me!
9. The very expensive mistake:
After I moved away, I paid over $1,000 for my now ex to come visit me across the country. On the last night of his eight-day visit, we had dinner, saw a movie, and went back to our hotel and had sex. Immediately after having sex, he told me he actually hadn't been into me for the past year and was ready to end our relationship. But THEN, had the nerve to say he still wanted to spend the rest of the night in the hotel with me, and still wanted a ride to the airport the next morning.
10. The very public Facebook message:
"We were in high school and had been dating for six months, when on my 16th birthday, I logged into Facebook to read all my birthday messages. And guess what I saw? My boyfriend had posted on my wall saying that he hoped I had a great birthday, but that we weren’t going to work out anymore. Needless to say, I cried all day and spent my 16th birthday in bed with ice cream and TV.
I learned years later that my dad was so mad when he found out, that he drove over to my ex’s house and shouted at him until my ex wet his pants. So, there's some justice out there.
—Victoria Arnold, Facebook
11. Parental permission:
When my boyfriend didn’t show up for our usual date, I️ tried calling and texting him. Finally, he sent me a text saying, "i’m sorry it’s over." This came as a surprise since we spent the entire night before saying "I love you" and searching for houses together. Cut to me, crying in a Best Buy parking lot, begging him to stay or at least tell me WHY he wanted to break up. That's when he told me he has to go ask his parents if we could stay together. Yes. He said he needed to ask his parents. He then drove off, came back, and said, "Yeah, they said no." We were 27 at the time.
12. The Craigslist sex solicitor:
My ex-boyfriend logged into his email through my laptop, which meant I received all of his notifications. Nothing out of the usual came up for the first few days. But then I started receiving all of his Craigslist notifications that showed he was soliciting himself for sex. When I confronted him, his explanation was that this method of cheating/breaking up with me was easier for him emotionally.
13. The plot twist:
My ex-boyfriend literally dumped me for my previous ex-boyfriend.
14. The incredibly unconvincing story:
After being together for a year, my ex-boyfriend told me he was gay. But then, the next day, he asked out my FEMALE best friend. They're still together, and I'm obviously not friends with her anymore.
15. A very merry Christmas:
After almost three years of living together, and after just spending Christmas with each others’ families, my ex decided he wanted to break up with me while having the ~where do you see us in five years~ talk. He said he didn't love me anymore and that he didn't feel that we could work things out. Which I totally understood, even though my heart felt like it was torn from my body. BUT, he had broken up with me on the first day of the month, and because he didn't have anywhere else to go, we ended up having to live together for that ENTIRE MONTH while we were broken up. It was the worst month of my life.
16. A telling STI test:
I was in high school and got talked into taking an STI test, even though I was in a monogamous relationship and didn’t want one. A week later, I was called back into the clinic and found out that I had chlamydia. That’s literally how I found out I was cheated on! To make things worse, when I confronted him, he freaked out and kept screaming that I had cheated on him, lol.
17. Casual PetSmart trip:
My last ex broke up with me right after I came back from vacation. He picked me up and we drove around so we could talk — or so it seemed. He started talking about how I was too nice, and that he had thought about breaking up with me through text, but that he thought I deserved a better break up (and all this other crap). When I looked around, I realized we had stopped at PetSmart. He was literally breaking up with me while he was running an errand!
18. An awkwardly formal breakup:
I got a text from my soon-to-be ex telling me to check my mailbox. When I went outside, I found that he had left me a typed letter saying he didn't love me anymore. It was really formal, and super awkward, and I really don't know why he couldn't just have sent me a text instead.
19. The momma's boy:
After SEVEN years together, he ghosted me. About a month later, I was "officially" dumped via a Facebook message sent by his MOTHER.
20. The Tinder fiasco:
The day before I left for a two-week trip, my ex-boyfriend and I were on our way to pick up takeout (that I paid for), when I took his phone to queue up another song. When I grabbed his phone, I saw that he had not only downloaded the Tinder app, but it was also the most recently used app on his phone, meaning that he had somehow used it in the short time between us having sex that morning, and leaving to pick up the food.
After the initial fight, which included me cursing him out and crying, I asked why he was on Tinder. His excuse was that he liked me, but he wanted to see what else was out there in case there was something better. He thought that with me going away for two weeks he would be able to explore all those possibilities!
21. You've got mail:
I had been dating a guy on and off again for about a year, when he suggested I move into his apartment for a two-week trial run. I was there for approximately one week, when I came "home" after making dinner and walking our dogs, to find that I'd gotten an email from him (he was a police officer and working the night shift at the time). In the very detailed, five-paragraph email, he broke up with me, yet again, with all the reasons why he didn’t want to be with me.
So I packed my stuff, did not burn down his apartment building, and left with my dog. I couldn’t believe that he broke up with me via email while he was at work, because he couldn’t come home and do it face-to-face!
—Vy Ma, Facebook
22. An especially unpleasant flight:
I got broken up with on an airplane, at the beginning of an incredibly long six-hour flight. We had to sit next to each other in total awkward silence for the entire rest of the time.
23. A FaceTime call to be remembered:
I called my boyfriend to say goodnight, when he suggested we FaceTime. He then, at 2 a.m., broke up with me during a five-minute FaceTime conversation, during which he had a girl in his bedroom the entire time. We had dated for nearly three years before that.
24. Roommate drama:
My ex and I were together for seven years, when we decided to move across the county together. We had lived together for six of those years and I believed that he was The One. We even went and designed my engagement ring together so I knew a proposal was coming. He was going to propose on our seven-year anniversary, but I found out about it and he canceled those plans.
One week later, he slept with some random person he met at a bar (I had no idea) and was late to our realtor appointment to buy a house. Just 24 hours after he cheated on me, we put an offer in together on our dream home. It wasn't until two weeks after we moved into that house, that he told me about the new girl and how we had to break up because he was madly in love with her. He then proposed the GREAT idea of us still living together as roommates for a while because he couldn't afford the bills on the house by himself.
25. A little too late, apparently:
We found an apartment, and were supposed to move down to Florida together. But he moved down six weeks before me because I had to finish school. I guess six weeks was too long of a wait, because during that time he decided to cheat on me. It gets worse... he chose to break up with me the day after I moved all the way down there and had unloaded ALL of my stuff into the apartment.
26. Family matters:
One day, he texted me saying that he didn’t think it was going to work out between us. And when I asked him why, he responded saying, "I’m in love with your sister." This guy still texts me once a year asking if I'm single. Wtf.
Responses have been edited for length and clarity.