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Read our Valentine’s Day horror stories and feel less alone

You'll laugh. You'll cry. But mostly laugh.


Marisa Kabas


Posted on Feb 13, 2015   Updated on May 29, 2021, 1:18 pm CDT

Having a spectacularly terrible Valentine’s Day is a rite of passage for people of all ages. Whether you first suffered Valentine’s Day-related humiliation at age six or age 26, the ghosts of V-Day past can haunt you forever.

This year, we asked the Daily Dot crew to share their most mortifying, gut-wrenching and/or knee-slappingly heinous Valentine stories, and boy, are there some doozies. We hope you can laugh at us just as much as we laughed at ourselves.

One Valentine’s day years ago I was exceptionally frustrated with my terrible boyfriend and walked past a stand of stuffed teddy bears. I tweeted, “No one should ever fucking buy their girlfriend a stuffed teddy bear, that is the cheapest shit,” or something like that. That night he came over holding a giant stuffed bear.

I just stared at him. He was like, “You don’t like it?” I’m like “No who would like a stuffed bear?

Selena Larson, Tech Reporter

When I was 15, I accidentally shit myself in a bowling alley on a double date with my parents because I was sick but really didn’t want to cancel. I’m pretty sure that was the first moment of the rest of my life.

When I was 15, I accidentally shit myself in a bowling alley on a double date…I’m pretty sure that was the first moment of the rest of my life.

— Nico Lang, Opinion Editor

Steve and I met freshman year of college in DC while working at the campus radio station. We ran into each other at the underage campus bar 12 days before Valentine’s Day and swiftly began dating. So when the big day rolled around, I didn’t expect much. But Steve told me, “Be ready at 7 and dress business casual.” He showed up promptly outside my dorm in a full suit and overcoat, carrying a box of chocolates, 3 roses, a giant stuffed animal and a card. My neighbors smoking cigarettes outside the dorm looked on in wonder.

He took me to the Watergate (yes, that Watergate) for a 3-course meal where we were seated next to a politician and were the youngest people there by 30 years. By meal’s end, I was over it and said I had to go home. When I flipped open my Sony VAIO and logged into Facebook, I had a request waiting: “Steve says you are in a relationship. Click to confirm.” I stared at it for a few moment, then called Steve to inform him that we were not in a relationship. The next day he showed up at the radio station when I was finishing up my midnight show, looking distraught. We broke up a few minutes later.”

 Marisa Kabas, Contributor

In fifth grade everyone gives Valentine’s Day cards to everyone, but I wrote some special declaration of affection on the back of Lisa’s.

A few minutes after cards were exchanged, her dispatched friend approaches me: “Lisa doesn’t like you. She thinks you’re an asshole.”

Dylan Love, Reporter

In 8th grade, I dated a mildly obsessive dude who bought me baby Jordans (like, $100 baby Jordans) for Valentine’s Day and my mom thought I was pregnant and so I accused her of thinking I was just fat and it was overall a really bad day. I remember crying at a Heather Locklear hair dye commercial. 

Another Valentine’s Day, I was in the jazz choir, and we would go around singing old jazz songs as singing Val-o-grams for other students and I had to sing one to this chick who my ex was dating and that sucked. 

Later that night, I had an ‘audition’ to work at Coldstone (yeah, they call them auditions), where they ask you to just ‘do something kooky for the group.’ All I could think of was singing that stupid Val-o-gram song and ended doing some horrible snapping movement with it. I ended up getting the job and really, really, really hated it and they would always be like “there, that’s the one who can sing” when we got tipped. 

“I remember crying at a Heather Locklear hair dye commercial.”

Molly McHugh, Tech Editor

My birthday and Valentine’s day are a day apart, so that usually makes it confusing for whoever I’m dating. Last Valentine’s Day, my then-girlfriend at the time bought us Viagra that she ordered online from overseas because I think I had mentioned that I wanted to try it, probably half joking. It didn’t ship in time, but as it turned out we were in Mexico on vacation so she just unromantically went next door to a pharmacy and bought some.

When she gave it to me, I didn’t remember mentioning that I wanted to try Viagra, so at the time it felt like some kind of really inscrutable criticism about my sexual prowess. (Admittedly it was kind of a weird idea, but I definitely did want to try it just for the hell of it.) Since we were in Mexico City I was having like the worst asthma attack ever from the air pollution, and on top of that I remember crying about something, so we didn’t ever take the Viagra on Valentine’s Day. But I did take it later because why not?”

Taylor Hatmaker, Tech reporter

So when I was in high school we had singing telegrams every Valentine’s Day. Basically, it was a bunch of the most popular dudes from the senior class going from class-to-class singing “Isn’t She Lovely” and “My Girl” and giving roses to girls (it was always girls who got them.) 95 percent of the time, these girls were dating upperclassmen, and 95 percent of the time, they were the hottest girls in the grade. Like, you would get one based on how hot you were. It was just, like, a thing.

Anyway, this happened from 7th grade to, like, 10th or 11th grade, and at one point I just had enough, like Jennifer Lopez in “Enough.” I wanted to get the fucking singing telegram.

So one year, I was dating this guy (who, in an M. Night Shyamalan-esque twist, was a legit psychopath), and either we were in one of our breakup-makeup cycles or I had pissed him off somehow and was too scared to ask if he would send me one, so I decided to buy an anonymous one for myself. It was like 3 dollars maybe, and you had to fill out a form. 

But when V-Day came, it never came to my AP US history class, which is where I’d told them to deliver it. So I had to go up to one of the hot senior dudes doing the telegrams and explain that I had ordered an anonymous telegram, it was for myself, but I didn’t receive it so I wanted my money back, but yeah, the recipient was me, it was for myself. Shockingly, I don’t think he was particularly weirded out by it, or else he was either too dumb or too polite to not laugh at me outright, but yeah, it was embarrassing.”

EJ Dickson, Lifestyle Editor

“I sliced my finger open during lunch sophomore year of high school and bled everywhere.

“I sliced my finger open during lunch sophomore year of high school and bled everywhere, after a foreign exchange student sent me an extremely thorny rose.”

Audra Schroeder, Reporter and Weekend Editor

“One year in college I made an elaborate scavenger hunt at my girlfriend’s apartment. She wasn’t big on romantic stuff, but I enjoyed doing things like that, and she’d humor me. She came down with a flu or something, and my clues were too difficult for her. So she was sick, felt incompetent, and probably didn’t want to be doted on anyway. She was a good sport about it, but it was the beginning of the end of me putting effort into being creatively romantic.”

Walter Coots, Designer

My first high school boyfriend dumped me the day before Valentine’s to get back together with his on-again, off-again ex who had convinced him that she was pregnant or something equally dramatic. I wound up spending Valentine’s watching The Producers in downtown Houston with the guy she’d dated to try to make him jealous; dude called that morning and said, “Well, I know you don’t have anything going on today either, so…”

Monica Riese, Entertainment Editor

My worst Valentine’s Day was when my boyfriend gifted me with a red velvet thong and than proceeded to pull his pants down to show that he loved me so much, he got a matching pair. We broke up the next day.

— Melanie Lessen, Executive Assistant

Photo via m01229/Flickr (CC BY 2.0) | Remix by Jason Reed 

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*First Published: Feb 13, 2015, 1:38 pm CST