Love & Sex

15 Horrifying Breakup Stories

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Sometimes you have to end things. But don't do it like this.

I was dating an older guy when I was a freshman in college. A bunch of my stuff ended up at his place, nothing major, but I’d let him borrow my VCR and a few other things. When I came back from Christmas vacation and went to his place, all of my stuff was packed up and neatly piled at the foot of his bed… where he was sleeping. Apparently, it was his way of telling me it was over. Even worse, my mom was waiting in the car at the time. — Robin


I’m the asshole in this story. I'd been living with my boyfriend in Taiwan for about a year, but had gotten into a bunch of grad schools in the U.S. As a token of love, I’d applied to uni in Taiwan — with no real desire to go. But somehow, I couldn’t tell my boyfriend that. Weirdly, because I loved him too much — and had I been going totally by my heart, I would have blown off Harvard to stay with him. I matriculated, bought a plane ticket, and still didn’t tell him. One day while he was at work, I packed my bags, with the intention of seeing him when he got home, then explaining, then leaving. Right when my cab rolled up, he texted to say he was stuck and would be a few hours late. So I just left. — Jenna


January 1, 2008 was probably an important date for a lot of people. I can imagine a lot of people making resolutions to quit smoking, stop eating fast food, or at least hold off drinking for maybe a week or so until the inevitable give-up. For me, that was the day my girlfriend made the resolution to change her life — by not having me in it. So January 1 became an important date for me too, because while I was at home on my Christmas vacation, my parents gave me a New Year’s resolution: “Stop crying so much.” — Ryan


I was cheating on my boyfriend of two years, Tim, with a guy named John. I really was planning on breaking up with Tim, but I hadn’t gotten there yet. One day, we were lying in bed when he made a joke. I squealed: "John!" That wasn't his name. I confessed I had cheated, and he broke up with me on the spot. A real two-minute whirlwind.  — Lina


After I decided to leave grad school and move to New York so that my girlfriend at the time and I could live together, she called and informed me that she wasn't ready to leave Cleveland and was breaking up with me. I convinced her not to. Two years and some serious maintenance later she ended the relationship, one I'd assumed would result in marriage, with a text message. I sincerely hope she has herpes. — Sean


My ex-boyfriend broke up with me thirteen days after I moved in with him, when we'd been dating for three years. It was right before Thanskgiving when he told me he’d already started dating his twenty-one-year-old co-worker. I moved out soon after, and took with me all of my stuff. I guess he'd been hoping to use it for Thanksgiving dinner  he was inviting his family over  because as I left, he shouted, "Thanks for ruining Thanksgiving!"  Three cheers for therapy. — Maggie



I got dumped by a girl via triangular folded note passed to me in the seventh grade. It was heartbreaking, though in retrospect, it sounds kind of quaint. — Ben


I was dumped over the phone in 2003 by a guy (a graphic designer, no less!) the summer between my junior and senior year. That it was by phone is not significant; what is significant is that it was during the fucking finale of Sex and the City. My roommate and I had befriended the only person with cable on our block, and we had gone over to watch it, only instead of getting my lady TV on, I was busy getting dumped on a stoop by some dude. Fuck that guy. — Anna


I'd been dating the same woman for almost three years, but it hadn't been working for almost nine months. I loved her, and I've never been good at pulling the trigger on stuff like this. As a result,  I spent a lot of time talking it over with a friend and coworker. After one such pondering session, smoking outside work, I went back to my desk, and feeling resolved, shot an email to him saying, "John, I decided. I'm going to break up with her this weekend." Only I didn't send it to him, I sent it to her — whether through an honest mixup or misdirected subconscious impulse, I'll never know. I do know she was pretty pissed. — Gil


I broke up with my boyfriend when it became apparent he was not only too dependent on me, but dependent on painkillers as well. One of the most memorable parts of entire breakup (which involved endless texts and calls on his part, to the point that I changed my number) was that his lawyer father tried to negotiate the terms of our separation. (We were in high school). He wanted me to stay in a relationship for another thirty days and "then see how I felt." Ridiculous. — Laura  


My boyfriend moved into a basement apartment a couple blocks from me and asked that I take care of his smelly-ass rabbit, "Jimmy Stewart," because his landlord did not allow pets. Mind you, Andrew never cleaned Jimmy's cage, fed him properly, or filled his water bottle on time, so the poor thing (until he moved in with me) was quite neglected. It would have been fine, except he was a narcissistic jerk, and I was getting sick of him. In a fit of final frustration, I drove to Andrew's office on Capitol Hill and delivered his rabbit to him at the Congressional office he was working in at the time. Affixed to Jimmy's cage were a few notes: It's over, I'm with stupid, and My owner is an asshole, don't date him. Of course, anyone reading those notes may have thought that I was in a sadistic relationship with a petite white rabbit, not Andrew, but still. — Alexis


My worst breakup was with my last boyfriend. Let’s call him Allan. We had been together for two and a half years and living together for one when our relationship ended. One night, during a particularly rough patch, I decided to go through Allan’s email to see if I could find an explanation for his recent weird behavior. Indeed I did. He wasn't just seeing someone else  he actually had another girlfriend. His ex, might I add. Perhaps, the title for "worst breakup" should go to Allan, though, because in one single night he got dumped twice. — Ashley


When I was in college, I'd dated someone for almost two years, but he'd never met my family. It had been so long that my family members were almost wondering if I'd made him up. Finally, our third Chirstmas together, he was to come home with me and meet everyone — until he confessed he’d been having a long and ongoing affair, the night before our plane left. We broke up, and I had to go home alone, heartbroken, and looking half like a crazy person who'd made up a boyfriend. — Wilson


Once a girl broke up with me to join the circus. Seriously. — Charlie