‘I tore up the rose she’d sent’: The secret stories from your most awkward break-ups

Confessions of relationships that went wrong


Breaking up is hard to do. Sometimes; other times, it’s just a bit awkward. You meet, they start rabbiting on enthusiastically while you sit, responding a beat too late to everything, knowing only too well that at some very imminent point, you are going to have to kick off proceedings with, “so, I need to talk to you about something”. By now, both you know what’s happening, but they’re going to make you say it anyway. Inevitably that’s not the end of it, and three days later they turn up at your front door, or write you a 4000-word confession that is half-love letter, half-character assassination.

In that spirit, I asked Tab writers from the US and UK to recount their most unpleasantly awkward break-up stories.


He wrote me a 4000-word confession that was half-love letter, half-character assassination.


Broke up with my school boyfriend at the end of my first term of university – obviously – but because it was long distance by this point, and I didn’t really want to have to go visit him to do it (or even worse: have him visit me), I did it over the phone. It was really mean and, fairly, he didn’t take it that well (read: he cried) but it was done. The next evening he called me to play me a song he’d written for me on the guitar, which was obviously excruciating. Almost worse was that I could hear his mum telling him to “stop, just stop now – give me the phone” in the background.


I was about to head off to university and wanted to go as a single man. So I waited until she returned from her holiday in Greece and did the honourable thing: I phoned her and told her I fancied someone else. A week later, I got my A Level results, decided actually I should probably pull out of Manchester, take a gap year and have a crack at Oxford. This made it quite embarrassing when a few months later I bumped into her on the train. She was equally shocked and said, “I thought I’d never see you again.” Didn’t even get into Oxford.


He turned up at my flat and suggested we “go for a drink”. As it happened we didn’t even make it for a pint, and were breaking up by the time we were standing outside the pub. It was raining, and I was holding his umbrella over both of us, meaning we were standing uncomfortably close to one another for a couple that was obviously about to break up. Anyway, we had a crap chat then one of those awkward hugs where someone gets their arm caught in the middle of the embrace, and I walked off with his umbrella, unthinkingly. Ten minutes later he was running back towards me – not to make a profession of love, in the downpour, like in Four Weddings, but to ask for his umbrella back. We had to say bye, again, awkwardly. Minutes later, a car drove past and sprayed me with a sheet of water – which I definitely thought only happened in films. I screamed. He definitely saw.


In Year 9, there was a girl in my school who was cute, funny and to my puerile eyes, perfect. We went out for a week in which we didn’t even see each other out of school. We held hands when we walked to Physics, but after the class was over and we walked from Physics to English, she got her mate Alex to dump me. I got sent out of English for calling her a “curly haired whore”.


Dumped on Valentine’s Day in my bedroom after a mate’s birthday at a bowling alley. He couldn’t work the lock on the way out so I had to come down and let him out of my house, where all my mates were just arriving for the after-party. They kept trying to get him to stay – assuming we’d just had a fight – while I cried harder and harder and he looked like he was about to have some kind of panic attack. Eventually my mate twigged and released him from the crowd. I drank most of a bottle of gin and threw up. Love sucks.


My boyfriend of four years broke up with me the summer before we were supposed to move in together our second year of uni. We couldn’t get out of the lease so we spent a year living together. Broken up. While he had a new girlfriend. 


Our school had a Valentine’s Day rose delivery system where you buy a flower for someone you were into in advance. I was emo – like everyone else – said it was mainstream, and didn’t think anything more of it. Fast forward to the weekend and she says that she’s got to stay home and can’t go into town. I go with some friends anyway and later see her holding hands with another guy in my year. I was too awkward to go over, but she dumped me over MSN later that night. Two days later is Valentine’s Day and it turns out she’d has other ideas: a rose turns up for me right in the middle of my first lesson. I couldn’t handle the trauma and tore it up.


When Justin asked me out at the eighth grade dance I thought it was a dream come true. But then things just went downhill very quickly because at 13, I already had the serious commitment issues which have haunted me ever since. It culminated when he couldn’t make it to the school fashion show I was modelling in because of a baseball game, but sent me a text saying, “I’m sure you looked beautiful today, wish I could’ve been there.” WHOAH, pump the breaks, Justin! I was overwhelmed by this “discreet” profession of his love, which to my mind constituted an attempted proposal and told him we needed to talk at school on Monday. In the middle of the playground, with a hip popped, my arms crossed and barely making any eye contact, I told him I felt suffocated: that things were just moving too fast and I didn’t think this was going to work out. That was the end of our three-week relationship. He now lives in California and works for Modern Family. I’m sure it was the crippling heartbreak that motivated him. I’ve essentially been single ever since.


I had been going out with a guy for a few months – based mostly on the fact I liked his Offspring hoodie (it was the mid-noughties, and this was a stupid reason because he took the hoodie off and I didn’t fancy him anymore). I didn’t want to break up with him though, mostly out of laziness and the fact that I was a stupid teenager who wanted a boyfriend, and I didn’t want to face up to the fact that I was deeply in love with his friend. As deeply in love as you can get when you’re fifteen and listening to Liz Phair a lot.

So he made the whole situation easier, but a lot more awkward, when he found my LiveJournal blog – the noughties were seriously such a hellish time – and printed it all out, in its entirety. All the things I’d written about his friend, thinking that a) nobody knew I had this tortured blog and b) I was a good enough writer as a tormented teenager to hide the fact that I was talking about him. We were sitting in a park and he handed it to me, pages and pages and pages of the stuff, all printed out (my mum didn’t even let me use our printer for school). I didn’t know what to do, so we sat in silence for ages, until he left, I put it all in my messenger bag, and we never spoke of it again. I got off with him a few times after that purely out of awkwardness, and then started going out with his mate after an acceptable amount of time had passed. He’s got a kid now to be fair, so at least he found love again. (Actually, also had an awkward break up with his mate, who told me he wanted to “finger other people” and dumped me. Cheers. Worth it.)


I broke up with the guy I was seeing during finals week. We were outside and it started pouring rain so we had to go into the nearest building, the library, which was packed and absurdly silent. So we had to whisper. Finally he stormed off into the elevator, but the door wouldn’t close right away so we just stared at each other until it finally did.


Not technically a “break-up”, but I once matched with a British guy on Tinder who was traveling through the States. I ended up agreeing to let him stay with me for a couple nights, and to be a good hostess, I texted to ask if he needed any toiletries (i.e. a manly scented body wash or something). He responded with, and I shit you not: “John Frieda Brilliant Brunette shampoo”. Since I also have brown hair and it was on sale, I obliged, thinking I would be able to use it when he left anyway. After he had left, I went into the bathroom and lo and behold, the fucker had TAKEN THE SHAMPOO WITH HIM. Later, he hinted that he wanted to see me again someday, and I responded with: “sorry, I don’t date shampoo thieves.” He left me the matching conditioner though.


My sophomore year, I started dating a guy who I met in poetry class (seriously). He was a faux-sensitive type, who liked carrying around skinny black Moleskin notebooks and debating the subtleties of dead British poets. I was obviously smitten, and let his moody writer vibe distract from how shit he was at sex. Four months later, naked in his skinny dorm bed (pre-coital), he told me matter-of-factly that our “time had run it’s course” and that he felt a “natural conclusion” to our relationship. And then he asked me to go down on him. I slammed the door in the dramatic ending only a poet deserved, and then wrote my final essay on an idea he had been mulling over for weeks – the best revenge for someone who thinks they’re original.


I got my mate to drop me off at my teenage sweetheart’s house so I could dump her. He waited outside while I went in, and I sat down on her bed and gave her the bad news, before leaving sharpish and getting in the car. When I got in he had a lukewarm tinny of Carlsberg waiting for me. I supped on it in between gentle sobs. We didn’t see each other again until she saw me walking down the street several months later wearing a hat that belonged to her. She yanked it off my head and pranced away into the darkness.


When I was 14 years old and Myspace was in its heyday, this skater boy who had a crush on me decided to show his love like any kid would – by changing his Myspace profile. But he didn’t stop with just my initials and a “<3” in the “About Me” section. His profile featured a black-and-white photo of my face and the page was quite literally dedicated to me. We dated for a few weeks, which is actually a pretty long time for ninth graders, and eventually broke up in the local skate park. I really just got bored of watching him skate around. Also he had a chihuahua that hated me. But because 14-year olds were not professional coders, when he went to remove the giant photo of me from his profile, he couldn’t figure out the correct bit of code to delete. So for the next five months, there was a tiny thumbnail picture of me in the right hand corner of his Myspace page.


I’d been going out with this guy for a few years, and he’d moved himself into my flat. I was having a girls’ night, and asked him to stay at his own (parents’) house. Little did I know, my girlfriends were planning to take me out for a drink to tell me that they’d found out he’d been cheating on me. All didn’t go to plan, as in he decided to literally follow us, uninvited, to the bar we went to. I was still oblivious, so they tried to sneak me back to my flat to break the bad news while he wasn’t there. They sat me down in the living room and started to try and tell me what happened.

But halfway through, he came barging through the door. Not just him, but TEN OTHER PEOPLE, most of whom I hadn’t even met. And neither had he. He’d literally brought a load of people from the bar back to my flat for an after party. So my friends took me into the spare room, locked the door and told me that he’d been cheating. I was so upset and didn’t even want to talk to him, so my friends went out and asked him to leave. But he refused to go, and instead sat on the sofa, while people were shouting at him denying everything. He basically refused to leave until we got proof that he cheated, which we did, and after about an hour he said he’d only leave the house if he could speak to me first.

All in the meantime these other random people in my living room were just there, watching awkwardly. The next morning my friend drove me back home, they packed up all my stuff and I haven’t stepped foot in that flat since that night.


After breaking up with my boyfriend, we had already booked a family holiday, so he decided to come along anyway as we were getting on fine as friends. He’d dumped me, so I told myself I’d stay strong and not go back there. But by the first night, we ended up getting together again. He told me he wanted to try again, and then tried to have sex. We hadn’t had sex while we were going out (but he’d tried) and again I told him I wasn’t ready and went back to my own room (he was staying in a room with my cousin). The next morning, I woke up and he’d conveniently decided that he didn’t actually want to get back together. He then booked a flight home, three days into the holiday, which I had to explain to my family.