46 Valentine’s Day Disaster Stories That Will Make You Want To Stay Single Forever

Shutterstock / Dzhulbee
Shutterstock / Dzhulbee

1. I ended up in the hospital after my hair caught fire

“We were out to dinner, and my fiance leaned across the table to romantically feed me a piece of dessert. But in the process, he knocked the candle over and onto my freshly gelled hair. I ended up in the hospital after my hair caught fire. However, we did get a free meal out of the deal—and I only had to endure a minor burn on my neck. I guess there’s literally too much fire in our relationship!”

—Christina

2. my dog died from chocolate poisoning

“My dog got into my Valentine’s Day chocolate that my girlfriend gave me, and later died from chocolate poisoning. I was 16, and had stupidly left the candy out.”

—Name Withheld

3. my boyfriend broke up with me by text

“Last Valentine’s Day, my boyfriend broke up with me by text. He messaged me that morning to tell me he’d been cheating for our entire relationship.”

—Hannah

4. my vajayjay must have been exposed to some kitty hair because it starts to swell up

“My college boyfriend gets his buddy to let us use his parents’ fancy New York apartment while they’re out of town. So we make dinner, get naked and start rolling around on the floor. But this friend’s parents have cats and I’m horribly allergic to cats. So I’m sneezing and my eyes are tearing up, but I am determined to ignore it all and have the best sex of my life. THEN my vajayjay must have been exposed to some kitty hair because it starts to swell up. I mean really SWELL UP. I’ve never seen anything like it before or since. Naturally, the V-day fun stopped there.”

—Nikki

5. a card that had another girl’s name crossed out with mine written underneath

“I once got a card that had another girl’s name crossed out with mine written underneath. Romantic.”

—Rebecca

6. I got a call from the county jail

“The guy I’d been dating, Clay, was totally MIA on Valentine’s Day. At first I was worried, but after not hearing from him all day I started to get pissed. That night I got a call from the county jail, asking me to accept a collect call from…Clay! He had stolen his parents’ brand-new car and they reported it to the police. Even though I have a thing for bad boys, I broke up that loser the next day.”

—Rachel

7. HE GAVE ME A MEMBERSHIP TO A WEIGHT-LOSS CLINIC

“I play rugby and my weight is required for protection and I also carry a lot of muscle. I was gobsmacked when I was presented with a slimming club membership from a date on Valentine’s Day. It took a lot of effort not to tackle him to the ground and throw him headfirst out of the door.”

—Naomi

8. HE CALLED HER AND SAID I DIED

“The first time meeting her she was extremely clingy and was already planning our wedding and how many kids we’re having – and I had only known her for an hour. Being 18 I wasn’t ready for this and she was scaring me a lot, getting very obsessed over me. She was giving looks of disgust to everyone who looked at me who was female. Fortunately, after the meal we went to get snacks from a corner shop and I accidentally bought a chocolate bar with nuts in – me having a severe nut allergy. I was rushed to hospital where I almost died but the next day I was discharged and went to my mate’s, where he called her and said I died. We’ve had no contact since.”

—Name Withheld

9. he thrust his face into my cleavage

“During the second date the man in question invited me to his house. After a semi-pleasant evening I was sitting on the couch and he was sat on the floor and we were watching a film. Without encouragement or warning he launched himself at me and thrust his face into my cleavage. I screamed and jumped up only to leave him in a heap on the floor with blood gushing from his face. Turns out the wire had protruded from my bra and got caught under his chin!”

—JP

10. another woman answered the phone

“Valentine’s Day, I called my boyfriend at college to see if he got my flowers and another woman answered the phone—at 8AM.”

—SJL

11. it was a prank and everyone was laughing at me all along

“In the 4th grade I had a huge crush on the most popular kid in class and everybody knew about it. Valentine’s Day approached and I found a piece of paper with a drawing of a girl labeled ‘Aisha’ with hearts all around the page and his signature. I start carrying the card all over the school with a grin on my face only to find out it was a prank and everyone was laughing at me all along. He then proceeded to ask my best friend to be his real Valentine. Terrible.”

—Aisha

12. edible underwear and a small vibrator

“I was a junior in high school and had been casually dating a guy for a few weeks. We weren’t serious and hadn’t gone further than second base when Valentine’s Day rolled around. I don’t remember how the night started, but I do remember being in his parked car when he gave me a gift. I opened a bag stuffed with tissue paper to find edible underwear and a small vibrator that fit over your finger. I took the edible underwear to school the next day, and my girlfriends and I had a good laugh after discovering how awful they tasted.”

—Liv

13. My husband made sure she got a present

“On Valentine’s Day, I found out my husband was having an affair with one of my close girlfriends. Her husband was the one who caught them and called to tell me as I was getting my hair done. Even better…I had given her flowers earlier that day because she told me she was sad her husband wasn’t going to do anything for her. My husband made sure she got a present, though, so there was that.”

—Jen

14. didn’t come to my place until 3am, covered in body glitter and drunk

“One ex went to a strip club for our first Vday together and didn’t come to my place until 3am, covered in body glitter and drunk and another gave me cellulite cream and miscellaneous Xmas lotions and lip balm from Avon his mom gave him. The only man who’s ever given me a nice valentine has always been my daddy!”

—Alexandria

15. I ended up falling on my face three times

“I took a girl ice skating but wasn’t as good as I remembered. I got skates a size too big so I ended up falling on my face three times before she finally suggested we go get some hot chocolate and pretend like that never happened. How I didn’t up with a bloody nose I will never know.”

—Kyler

16. he proposed on the second date…at olive garden, no less

“I was on a date with this guy, and we went to Olive Garden because I mean, hey, it’s Olive Garden. We went through the whole dinner. Everything was going great, you know. We were going to go see a movie. It was all going to be a good date and then dessert came. He was checking his phone and my dessert was set in front of me and there was an engagement ring on it. This was our second date. I grabbed my stuff, and I booked it to the bathroom, and then I just went out the front door. I never came back because I was like, dude, who proposes on the second date? I don’t even think he knew my last name.”

—Taylor

17. He told me on the phone that he wanted a divorce

“My worst Valentine’s Day ever was Feb. 14, 2002….I got a call while still at work..and it was my husband. He told me on the phone that he wanted a divorce and would be moving out that night. When I got home from work he was partially packed. He didn’t move that night. We actually went to dinner with my parents and my children for the holiday and he moved out the next day. A Valentine’s Day I will never forget.”

—Name Withheld

18. That night I saw him out with another woman

“My worst Valentine’s Day ever was two years ago. I was dating a guy that I’d been off and on with for three years. I bought him an expensive pool stick, a bag to go with it, ordered him a dozen roses, and paid to have a poem written for him. I had planned the whole evening out already. He called me that morning and told me that he had too much going on in his life and didn’t have time for a girlfriend. Especially a serious one. So I decided that I would go out with a friend to try not to think about it. That night I saw him out with another woman.”

—Name Withheld

19. We broke up the next day

“A new guy surprised me by planning the perfect Valentine’s Day date: a romantic dinner followed by fireworks show on the beach. Everything was great until the check arrived. He asked me, “Should we split it or do you just want to pay for your meal?” After dinner we took a walk on the pier. He bumped into a girl, who was obviously his ex-girlfriend, and after talking and laughing for about 20 minutes without including me he finally said, ‘Oh sorry, this is my friend, Kat.’ We broke up the next day.”

—Katrina

20. I almost choked on my drink when our waiter arrived

“After secretly dating two guys — Dan and Joe — for a few months, I told Joe I didn’t want a relationship, so that I could get serious with Dan. On Valentine’s Day, Dan took me out to dinner, and I almost choked on my drink when our waiter arrived. It was Joe! To make matters worse, Dan ordered a dish with béchamel sauce, which he loved. He gushed to the waiter, a.k.a. my ex, ‘If she could cook like this I’d marry her.’ I wanted to die.”

—Cristina

21. I pulled off Abe’s head and kicked that boy to the curb

“After a long dry spell, I was psyched to finally have a new guy in my life so we could spend Valentine’s Day together. Call me corny, but I was hoping I’d get flowers or chocolate — you know, what every girl wants! Instead, he gave me an old Abe Lincoln Bobblehead that looked like it came from the bottom of his closet. I honestly didn’t even know what to say, so I just mumbled “thank you.” After a few more bad dates, I pulled off Abe’s head and kicked that boy to the curb.”

—Adrienne

22. Krista spent the night with my guy!

“My boyfriend Matt and I didn’t have any special plans for V-Day, so he decided to have a few friends over for an impromptu get-together. I was a little pissed that he invited Krista, a girl I suspected had a thing for him. I played it cool until later that night, when he admitted that he had cheated on me with her a few months before. When I confronted her she denied it, but later I heard her ask Matt, “Why did you tell her?!” After a big blowout, I left the party and Krista spent the night with my guy!”

—Ciara

23. a $200 bill and a bad, bad taste in my mouth

“Runar and I met at a coffee shop with friends. At first sight, I got swoony. He had blond hair and muscles. Lots of muscles. The kind a guy gets from doing manly things like shoveling snow. He said I was beautiful. That usually works for me. By our third date Runar confided he was bouncing around the idea that we should get married and have a couple of kids. At our three-month mark, Valentine’s Day rolled around. Off we went to an expensive French restaurant, candlelit and decorated with festive hearts and pink ribbons. During the main course he asked me if I’d ever had sex without a condom. Sure, I said, thinking everybody has at least once. I started to say it was a long time ago, but he was already in a road rage. His eyes blazed, he threw his napkin on the table, knocked over his water glass, left it there and stood up. The chair made a horrible scraping sound against the floor. Everybody turned and looked at us. He screamed, ‘You put me at risk!’ Runar stormed out of the restaurant leaving me with a $200 bill and a bad, bad taste in my mouth.”

—Dorri

24. my college boyfriend broke up with me

“On my worst Valentine’s Day, my college boyfriend broke up with me. I deserved it but I didn’t see it that way. I staggered out of his apartment. It was cold—thank you, February—and my hands were shaking. I couldn’t unlock my bike, which was chained to a parking meter. I stood there, crying, and finally a man with a beard and a wool cap stopped and unlocked the bike for me. He was my Valentine’s Day hero. Except then, of course, I had to ride home.”

—Emily

25. SECRET ADMIRER

“My mom recently sent me a package of stuff she’d saved from my elementary school days. In the package was a red envelope with a valentine inside from ‘Your Secret Admirer.’ I opened it up, my heart beating. It said: ‘I really like your handwriting.’”

—Hannah

26. he’d shot himself in the leg

“I met a guy in our local supermarket and we got talking. We arranged to meet up a few days later but he phoned me the night before and told me he’d shot himself in the leg and was in hospital so couldn’t make our date! I visited him in hospital and we did eventually get out on our date but we both agreed that it wouldn’t work and I never saw him again.”

—Ros

27. twenty-something-year-old girl sleeping like a pig beside a pool of her own vomit

“This happened years and years ago, but we went drinking on Valentine’s Day. I can’t really hold my alcohol but I kept drinking anyway. So how it ended was me and him stumbling out of a cab at the carpark beneath his block, throwing up and me falling asleep right there at the carpark. Obviously don’t remember any of this, but picture this: 20-something-year-old girl sleeping like a pig beside a pool of her own vomit. My then-boyfriend (now husband) could not wake me up no matter how hard he tried, and was too drunk to lift me. So he called his father down to carry me up.”

—Name Withheld

28. yes, he’d been cheating

“One Valentine’s Day, there was a huge snowstorm. My boyfriend called to urge me to stay at work (where my boss was offering to people up in the nearby hotel) rather than risk driving 35 miles home. But I had a special V-Day meal all prepped, and I insisted on going home. When I got there, I got stuck on the unplowed one-way road next to our apartment, and I called him to see if he’d help dig me out. His response was a very startled “Where are you?!” I assured him I was safe — and just outside. He yelled at me for risking it. And then I saw him … sneaking out of a house a block away … and it turned out that yes, he’d been cheating. Worst part: he went back to her place after our “discussion” and spent the night there.”

—Kathleen

29. Please read: Very important

“About a year and a half after a boyfriend broke up with me, after not hearing from him for all that time, an e-mail from him popped into my inbox on Valentine’s Day with the headline ‘Please read: Very important.’ My heart jumped, as I began thinking that he had been missing me and had chosen this most significant day to express his regret at ending the relationship. But when I opened the e-mail…it was a mass-mailing he had sent out, rallying support for keeping the Pledge of Allegiance in schools!”

—Jane

30. she told me that she was not ready for the love

“Told my ex-girlfriend that I love her at evening of Valentine’s Day before kissing her goodbye. Got the pull away and she told me that she was not ready for the “love.” The night ended in silence, we broke up 3 weeks after that.”

—John

31. Caught my boyfriend texting his ex-girlfriend how he still loved her

“Caught my boyfriend texting his ex-girlfriend how he still loved her, he was pointed directly to the door. No questions asked.”

—Cari

32. flower mix-up

“I had flowers delivered at work from my then boyfriend. The card read: 
’Brandy, You have my heart
Happy Valentine’s Day.
Love always, Jay.’
My name is Amanda.
Come to find out local flower shop delivered her flowers to me and my flowers to her. But he filled out the cards, so in the end it was his own mix-up.”

—Amanda

33. he sits bolt upright and punches me in the nose

“I was a freshman in college and my boyfriend wanted a blowjob. Though I’d done ‘stuff’ before, I was still learning how to round the bases. A cool older girl offered a lot of advice about oral sex. ‘Pretend his junk is an ice-cream cone,’ she said. ‘Play with his balls.’ And also: ‘Wake him up with a blow job — he’ll love it.’ I decided to proffer his first blowjob as a gift on Valentine’s Day. The night before V-Day I am so excited that I just lie there awake all night. Waiting for him to fall asleep. Waiting for him to stay asleep. Waiting for him to wake up. Finally, as daylight breaks and he is stirring, I go for it. He’s hard and gets harder in mouth. He seems to be into it when all of a sudden he wakes up in shock and — in one lightning-fast reflex — sits bolt upright and punches me in the nose. Really hard. Despite what pornography may suggest, some men do not react well to being woken up to sex. So we go to the campus health center, where we spend the day having my nose reset and explaining that it wasn’t domestic violence. For dinner he takes me to Taco Bell, where we spend the meal arguing about whether I am a sexual predator. To this day I get really nervous initiating morning sex, so I’ll sort of stare into his face while rubbing his thigh until I end up in what, I am told, has become my signature sex move: hand jobs with weirdly intense eye contact. My nose is still bigger than it used to be.”

—Name Withheld

34. There is nothing sadder than a flaccid hand job

“I met a guy singing karaoke at a bar, and he texted something like “Let’s hang out on Friday.” And I thought, What a bold move! Valentine’s Day first date, why not? So I met him at a bar during a snowstorm and ended up back at his place pretty early, maybe 9 p.m. We walk in and his brother is super stoned on the couch, three seasons of Bones DVDs scattered around him, having a marathon. Okay. So we go into the kitchen and my date pulls out a bong that is, like, as tall I am. I don’t smoke that much weed, but we’re there, so I smoke it and get so high that I can’t see straight, at which point he puts on a CD of his own really bad folk-acoustic band. It’s so loud, and I’m so high, and finally I say, “Let’s go to the bedroom,” just to get away from the music. So we start making out, mostly to kill time, because I’m way too high to drive home. Then all of a sudden, he is completely naked. I am completely clothed. I basically ignore his nudity, which is easy because it’s a pretty limp situation. He’s on top of me when he gazes deep into my stoned eyes and says, “I haven’t been able to keep it up since going on anti-psychotics after my psychotic break during an LSD trip.” I’m not kidding. I wonder whether a man like that should smoke so much weed, and give his flaccid dick a hand job. There is nothing sadder than a flaccid hand job. It was laborious and mechanical. I listened to Bones the whole time. Then I lie there for 15 minutes, and though I’m still too high to drive, I pretend I’m fine and go out to my car to sober up alone in the freezing cold, because it’s better than the scene inside. I sat there in my car, doing nothing, for half an hour. He still sends me Facebook invitations to see his band play.”

—Name Withheld

35. two days after a drug overdose

“My rock-bottom Valentine’s Day occurred two days after a drug overdose. To prove I wasn’t suicidal, I showed my doctor the dress I’d purchased to wear on Valentine’s Day. My poor boyfriend brought roses during visitor’s hour on February 14, but roses were not allowed in our rooms (in case we whittled them into weapons? I never found out), so I was only allowed to look at them through the glass of the nursing station.”

—Name Withheld

36. alone and broke

“I think [my worst Valentine’s Day] would be buying non-refundable tickets to go see my boyfriend in Georgia. We’d been doing the long-distance thing for a while and I had plans to go visit him. And then, about a week after I bought the tickets, he just stopped talking to me. Forever. No response to my texts, never answered my calls or emails. Nothing. So I spent my Valentine’s Day alone and broke because I had these tickets I couldn’t use.”

—Name Withheld

37. When the door opened, it was some guy

“I’d been dating a girl for awhile and wanted to surprise her with a balloon and flowers. I spent all day making the elaborate plans and getting everything I needed. I kept trying to call her all day, and she didn’t pick up. I didn’t think much about it, maybe I should have…Anyway, I get everything loaded and I head over to her apartment. I saw her car and the light was on. So I got the stuff and knocked on her door. When the door opened, it was some guy, and she in the back saying, ‘Who is it?’ Shocked, I quickly made up some lie that I had a delivery for some fictitious name and must have gotten the wrong address … I drove away. I spent the rest of the night at a park, sitting in my car and listening to a ball game on the radio, not really reacting or anything. The balloons and flowers remained in the back seat of my car until the flowers died and the balloons deflated. I never talked to the girl again.”

—Name Withheld

38. I think this is going to be it for us

“I had been dating this guy on and off for about four years. We had a history of having really unfortunate Valentine’s Days. I was usually at school and we missed the chance to hang out or we ended up fighting about how I couldn’t break away from school to come home for the event. Finally during my senior year of college, Valentines’ Day fell on a Saturday so I went home. I had spent the week picking out a perfect gift and even paid extra to have it shipped to me on time. I made the hour and a half drive home to spend the weekend with him. We had a pretty good day, relaxing, and at the end of the night he walked me out to my car so I could drive back to school. I had just gotten in my car and Derek was leaning on the door to say good bye. I was just about to say that I’d had a great time when he said ‘Well, I wanted us to finally have a good Valentine’s Day, and we did. But I think this is going to be it for us,’ and then he closed my car door.”

—Courtney

39. my husband went out for a pack of cigarettes and never returned

My husband, a professional athlete from Sydney, Australia, and I were married in September 2006 and we lived in NYC. In the summer of 2007, I gave birth to our son, Chille. He had a heart defect and endured two open heart surgeries before he was 8 months old. We lived in the ICU for months on end. On Valentine’s Day, 2008 my son was in the Emergency Room, hanging on for dear life and in critical condition. My husband was out of town for a business trip and was returning on Valentine’s Day. I had no cell phone reception and just left a message telling him that when he returned, to please just rush in to the hospital, that they were admitting our son to the ICU. Before our son was transferred, I stepped outside to check to see if he had called, if he was back in town, yet. There was one message on my phone. It was from my husband. He message said ‘Listen carefully. I’m in Sydney. I can’t take it anymore.’ When I returned to our apartment later that day to take a shower and get some fresh clothes for the hospital, I saw just what ‘I can’t take it anymore’ meant. Every trace of him was gone, every drawer emptied, and every bank account, including our son’s $30,000 college fund was drained. I learned he stopped paying the rent and I had no money and a baby in critical condition laying in the children’s hospital. On Valentine’s Day, my husband went out for a pack of cigarettes and never returned. Only he didn’t smoke and apparently the pack was in Australia. Oh yeah, and one last thing. My birthday is February 15.”

—Ali

40. seven pounds of cream cheese

“I was supposed to see a guy I had just started dating. I baked his favorite dessert—cheesecake with, like, seven pounds of cream cheese. He DUMPED me on Valentine’s Day. I took the cheesecake to work lest I eat it myself to drown my sorrow and on the way there I was in a vile accident. They had to cut a hole in the roof of the car to get me out. I was mostly out of it, but asked the ambulance guy on a date and offered him my cheesecake which was now full of broken glass and smeared all over the backseat. For some reason he said no.”

—Eileen

41. I spent it in the bathroom of my hotel room crying

“I once saved all my money to fly from Los Angeles to Vancouver to see a man I was in love with. On the plane, I brought with me a boom box, a CD mix with all romantic songs on it, candles and incense. Once I got to Vancouver, I set up the hotel room in a beautiful way with all of the things I brought. The man then showed up two hours late with another woman! He later told me he thought we were ‘just friends with benefits.’ All this, after 10 years of being lovers off and on. It was the worst Valentine’s Day of my life. I spent it in the bathroom of my hotel room crying. I couldn’t get back on that plane to LA fast enough. To this day, I refuse to go to Vancouver.”

—Jen

42. he was only pulling a prank on me

“One time, in middle school, my biggest crush asked me to be his girlfriend. After that, I started sending him cute glitter texts saying how much I loved him and missed him. A few days later, right before Valentine’s Day, he told my best friend to tell me he was only pulling a prank on me because he wanted to see what would happen. Life sucked.”

—Carolynn

43. a very awkward moment

“I had a very awkward moment when I slipped an anonymous Valentine to my crush George and he showed it to everyone in the class. They all recognized my handwriting so they knew it was from me. I tried to front like it wasn’t really from me but that I had written it for a friend. No one bought it, of course.”

—Caroline

44. stood up by a mystery admirer

“I was sitting in history class on Valentine’s Day when I got a weird text from a number I didn’t recognize asking me to be their Valentine. I had no clue who it was, so I asked. He said we had met before, but didn’t give me any more details. After hours of texting back and forth, I was dying to know who my secret admirer was. I agreed to meet up for a blind date at a coffee shop, but took a ton of safety precautions (including telling all my friends where I was going and letting the barista know I was on a blind date). I got to the coffee shop and was so excited. Time ticked by. A half hour later, I realized I had been stood up… on Valentine’s Day… and I didn’t even know by whom. The next week, the same anonymous number teased me about getting stood up. The whole experience was such a bummer.”

—Lauren

45. I burned my present to a crisp

“One year, my husband thought he was being really clever by hiding my present in the oven. It would have been a nice surprise – had he not forgotten to tell me before I started cooking breakfast, burning it to a crisp.”

—Fiona

46. picking out bits of bread roll from my teeth

“It was my first date wearing braces (the chunky metal-train-track-kind) and I admit I was a bit nervous especially as we were going out for dinner. My date insisted we went to a burger restaurant and try one of those mighty challenge ones stacked with onion rings, cheese and everything you can imagine. A massive burger was the worst possible thing to eat with my new train tracks and there I was trying to eat gracefully but picking out bits of bread roll from my teeth. I tried using a knife and fork to tackle the rest of it but failed miserably. I couldn’t face him again after that date. ”

—Claire TC mark

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