14 People Share Their Cringe-Worthy Valentine’s Day Stories (That Will Make You Feel Better About Your Own)



“It was about to be my first ‘single on Valentine’s Day’ in a really long time, and I was not stoked about it. It’s not that I even cared about the holiday, but it felt like this giant reminder of my break up everywhere I went. Like Hallmark was mocking my sorry ass. So, I did what all miserably sad people do. I decided I’d download Tinder. I started messaging back and forth with this one dude. From his pictures, he seemed cute and athletic. We shared a love of paddle-boarding and other aquatic sports. It was a fun, flirty distraction. I didn’t even have an intention to meet up with him, but then he asked if I wanted to hang out on Saturday. And Saturday was Valentine’s Day. We both kind of laughed about it, said it would be low-key and not a big deal. He said he and a bunch of friends were going out to a bar, and that I should join. This was my first date since I’d split with my ex and I was trying not to freak out, but I was. I get to the bar, see my date, and yes, he’s very cute. But guess who I see sitting next to him? My ex. Because apparently they are friends.”

— Viv, 26


“In high school, I was very stupid (as most teenage boys are.) I was hanging with a bunch of friends because one of my buddies was dumped the day before Valentine’s Day. We were underage, so we didn’t obviously have a ton of access to alcohol. But we were determined to get drunk and lament over our sad love lives. One of our friends found a gallon of mint extract in his house and told us all it had methanol in it, and therefore we could probably get drunk of it. We drank it. It was disgusting. We did not get drunk. And we spent all night throwing up.”

— Brandon, 21


“In 7th grade I wrote a Valentine’s poem for my crush about wishing I could ask him to be my Valentine but I was too shy and signed it ‘anonymous.’ I left it on his chair before class when no one was in the room. When he found it he was with a popular girl. They read it together; she yelled ‘Gross, I bet Annabelle is the one who wrote it!’ They both proceeded to ‘eww’ and he threw it in the trash can.”

— Annabelle, 29


“An hour before going out to a fancy V-day dinner, I found out my boyfriend had been cheating on me for more than 6 months. His phone rang. I answered it because he was in the shower and it’s not uncommon for us to do that. I thought we had no secrets. It was an unsaved number and a girl wondering who the hell I was. Needless to say, I canceled our reservations for the night.”

— Fatima, 25


“One time I made Geoff Bird a homemade Valentine’s Day card and he gave it back to me and said ‘No thanks'” I was 9.”

— Catherine, 24


“We had tickets to a Broadway show. I ate something that disagreed with me and shit my pants while running to the bathroom. And to make matters worse, I was wearing a thong.”

— Lisbeth, 27


“Freshman year of high school dateless me designed and printed up a bunch of ‘badges’ with Spike from Buffy The Vampire Slayer on them. They read ‘Love Bites.’ I tried to give them out to other single people. They were not popular.”

— Maya, 28


“Last year I spent a few hours excitedly waiting for my bf to visit me on Valentine’s Day. I made him chocolate covered pineapple and wrote him a card telling him I loved him. When I asked what he got me he replied- ‘nothing.’ Thinking he was kidding, I start laughing like a maniac along with my sister. After that, just dead silence and awkward glances were exchanged. Then he asks ME to make dinner reservations for us. Glad we broke up.”

— Tina, 20


“It was amazing…until she switched it up and tried reverse cowgirl, totally overestimating her abilities. We ended up in the ER all night because I was convinced she broke my dick. We soon stopped seeing each other after.”

— Christian, 32


“I was stood up. Not the worst thing in the world, but there’s something extra-cringey when it’s the one night you are SURROUNDED by lovey-dovey couples and the waitress just keeps looking at you like you’re a wounded puppy.”

— Kenny, 29


“My ex came to visit me at work at my old restaurant job one Valentine’s Day with an adorable teddy bear and Russell Stover chocolates. I made some kind of remark about how I didn’t like Russell Stover chocolates because they’re too sweet (in retrospect, I think I was also thinking of Walt Whitman chocolates — great poet, crappy chocolate), and like wildfire my terrible reaction to my boyfriend’s sweet gift turns into the laughing stock of the entire restaurant. A decade later, old work friends still bring up to me what a snob I was. I’m always like, ‘I’ve repented enough, guys, okay!?’

And I still have the teddy bear. I’m really not a jerk, I swear.”

— Skylar, 26


“Last Valentine’s Day I was single and I was like, ok this day will suck but it will be fine. So I decided to have a treat yo self day and just do what I felt like doing. I got a giant bottle of wine and some snacks, lit some nice candles, and laid on the couch reading Twilight. I had an agreement with my roommate (who was newly in love) that she wasn’t going to come home that night because I didn’t want her shoving her awesome relationship in my face. WELP. I am just settled into Twilight when her and her hot af boyfriend pop in to see how I am doing. and I was like, ‘Hi, I’m a loser reading Twilight and drinking alone.'”

— Maureen, 28


“For Valentine’s Day I wrote my boyfriend of three years a song about us growing old together. The next day he Skyped me asking to be in an open relationship.”

— Deena, 24


“I take Ambien to sleep, and on Valentine’s Day I had a few glasses of wine. It was a pretty average day. I was seeing someone, but casually. We had a good date. I went to bed, took my Ambien. I guess the alcohol + Ambien was not my best idea because I woke up with zero memory of calling my ex boyfriend 5 times in the night. Oops.”

— Lola, 31 Thought Catalog Logo Mark

About the author

Ari Eastman

✨ real(ly not) chill. poet. writer. mental health activist. mama shark. ✨

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