Valentine's Day Horror Stories to Make Yours Feel Better (2024)

Venture into any town centre on the evening of Valentine’s Day, and you’ll see the full spectrum of love, as restaurants are packed to the rafters with people trying desperately to have their special night together.There’s the star-crossed lovers performatively snogging each other’s faces off in booths; there’s the long-term couples sitting across from each other in painful silence, occasionally commenting on the garlic mushrooms; and then there’s the singletons, usually in the pub next door, frantically glancing around the bar in hope of the ultimate meet-cute.


Yes, for those who dare to observe it, Valentine’s Day – if not navigated shrewdly – can be an abject disaster. But how bad can it be exactly? We decided to speak to our readers about their most catastrophic attempts to find, transmit or escape love on the most romantic day of the year. So, if you’ve always found it to be a sickly sweet mess, then you may find comfort in these tales.

‘He hired a barbershop quartet, it was excruciating’

“I was 17-years-old and it was my first Valentine’s Day with my boyfriend. It was my first relationship and he took me out for a meal at our local pub in Croydon.“I thought flowers and dinner would have been more than enough, but just as we started tucking into our meal, four old-ish men in red tuxedos, bow ties and boater hats walked in. I nudged him to look because it was hilarious, but then they came to our table. I felt terrified as I realised what was about to happen. They introduced themselves in front of all the other diners, handed me a teddy bear, blew a little tuning whistle and started singing.

“I felt like my face was on fire… I couldn’t actually believe it was happening, it was so surreal. They sang three songs and people were turning, watching and laughing – the attention was excruciating. It was typical barbershop quartet music, too. Each time they finished singing a song I'd feel relief, only for them to start up again. It was hard to recover afterwards, and I was definitely in shock for the rest of dinner.


“Looking back, I think he may have been inspired by an episode of Friends where Ross hires a barbershop quartet to sing for Rachel at her new workplace. It’s weird because Rachel hates the quartet in the show, and it's very much framed as a possessive move by Ross. So I have no idea why he thought it was a good idea. I’ll never forget those red tuxedos!” — Leila, 30, France

‘I woke up next to my Valentine’s date; she said her husband was on his way home’

“I had gone to meet a girl for Valentine's dinner but there were red flags early on. When I went for a cigarette she said, ‘It better not be drugs.’ And then she started talking about her husband, which surprised me as I thought she was single. I was very unsure, but we ended up going back to hers anyway.“She had awkward energy when we got back, so I helped us both to a bottle of red wine from the fridge. But when I opened it, the contents went flying everywhere, including all over her very new, very white sofa. She went absolutely ballistic; screaming, shouting and demanding I buy her a new sofa. Weirdly, we ended up having sex anyway and I stayed over. But I woke up to news that her husband was coming home and wasn't best pleased about the sofa.


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“I was freaking out, so I chucked what money I had on the kitchen table and legged it. They're probably both fuming, but thankfully I got out before he got back so I'll never know.” — Dave, 32, London


‘The staff staged a coup to help me escape’

“I went on a first date to a bar on Valentine's Day, and the guy was just awful. He kept answering his phone instead of talking to me because, apparently, he had ‘clients in the U.S.’ and a ‘business deal’ to sort in LA. His massive watch gave me the ick, too. It wasn’t going well, but he tried to be flattering. At one point he said: ‘It’s cheesy to meet on Valentine’s Day but it could be a cute story to tell people about how we met.’“There were three young waiters at the bar and, when my date went for yet another phone call, one of them said, ‘We all think you’re too good for him.’ We decided we’d have to do something if he left the table again. After the third phone call, I told the waiters I was done with his sh*t. One of them stood near the terrible date to check he wasn’t coming back, and the other two discreetly snuck me out of the restaurant via a side door, like a celebrity trying to avoid the photographers.” — Jenny, 25, Camberwell

‘I flew overseas to get away from my boyfriend, then he followed me’

“I had booked a romantic Valentine’s getaway to Jersey with my boyfriend. But after a final massive row, I decided our relationship was doomed. I cancelled his flight and went on the trip alone.“When I arrived, I had another problem: Fending off the advances of a persistent medical sales rep at the hotel bar. He was so relentless that, on the second evening, I ate dinner in my room to escape him.


“The next day, on actual Valentine’s Day, I was determined to salvage what was left of my romantic getaway, so I went on a solo trip to the zoo. That evening, a sympathetic couple took pity on me and I ended up having my romantic meal with total strangers.


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“I had been avoiding my soon-to-be ex’s calls and messages, and instructed the hotel not to connect him to my room, but then I received a tip-off that he had decided to follow me and was getting a flight out. I flew back immediately, and got a call from him when I was home, saying he was at the hotel. He seemed taken aback that I had gone.” — Kara, 26, Sussex

‘He got my name tattooed on his chest’

“He first approached me in a bar. He was two years younger at the time, in his early 20s. I didn’t have the skills to put up healthy boundaries so I often ended up speaking to people even if I didn’t particularly want to. At first I thought I’d be polite as I kinda felt almost sorry for them, but eventually I just wanted them to leave me alone. We never dated properly, just went out for a couple of meals.“My friend persuaded me that if I met them one last time he would leave me alone, which, in hindsight, was very naïve of me. I met him and that’s when he showed me he’d got my name tattooed on his chest as a ‘present’ for me for Valentine’s Day. When I said I didn’t like it he took that as rejection and got angry, posting loads of fake stuff about me all over the internet.“I actually felt physically sick that they had taken something very personal from me by having my name tattooed on his chest. I felt that in some way he had part of me on him. In fact, it upset me so much that years later I changed my name.” — Lena, 32, Birmingham

‘I spent six hours in the cinema, plucking up the courage to finger my girlfriend’

“I went to the cinema when I was 14 or 15 and we watched My Bloody Valentine, the 3D film about murderous coal miners. I fingered the girl I was with in the back row because it’s what you did in those days, but I didn’t enjoy it because I’m gay – I was still trying to be straight and was in denial.“We kissed, but nothing else happened during the first film, so we booked to see another film straight after. It took me nearly six hours of films to pluck up the courage to use the finger. It was probably just as awful for her as for me, but it got both of us creds when we told our friends at school the next day.” — Will, 29, Bethnal Green

Valentine's Day Horror Stories to Make Yours Feel Better (2024)
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