On Valentine’s Day we celebrate love. Romantic love, usually. Self-love, sometimes. And now, in the name of that powerful bond that exists between “misery” and “company,” we celebrate 11 real horrifying stories of hopeless humiliation, broken hearts, broken noses, and the most ill-advised first date of all time — all of them occurring on Valentine’s Day. Enjoy your love of Schadenfreude through these real — and really terrible — tales from the Cut and our miserable-but-magical friends.
1. She Broke Her Nose During a Blow Job
I was a freshman in college and my boyfriend wanted a blow job. 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 blow job 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.
2. Mistake Cake
I made my high-school boyfriend a cake that said “Happy VD!” We never had sex.
3. The ADHD Love Triangle
One time a guy said “I love you” on Valentine’s Day and I replied, “Oh, so you waited until Valentine’s Day to tell me? How manipulative.” In my defense, we were walking out of a screening of In the Company of Men, and he said it after admitting that (a) he hadn’t broken up with his girlfriend and (b) he couldn’t hold my hand because “we’d get caught.” So he said “I love you,” then started to cry. Then he said, “I’ve never said ‘I love you’ to anyone before.” Maybe it was the movie’s influence, but I kept walking and called out, “Sorry, how many cards are you going to play tonight?” Still one of the most romantic nights of my life. I finally said “I love you, too” when he caught me stealing his Adderall.
4. First Date From Hell
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.
5. Rock-Bottom Valentine’s Day
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.
6. Check YES or NO or OOPS
In the fifth grade I had a huge crush on a boy named Charlie and made him one of those cards that asked, “Do you like me? Check YES or NO.” But I’d filled it with, like, word searches and riddles to figure out my identity, even though it was obvious because I was staring at him the whole time. I was so entranced watching him solve his Valentine that I wasn’t paying attention as I tipped so far back in my chair that it slipped, and I fell, and my finger was crushed between the chair and a filing cabinet. I immediately started sobbing and ran to the nurse. If I remember correctly, there was a field trip to the high school to hear their band play that day. I missed the bus because I was at the nurse. By the time I returned, Charlie was gone.
7. Singing to Herself
When I was in high school we had singing telegrams every Valentine’s Day. Basically, the most popular senior guys going classroom to classroom singing “Isn’t She Lovely” and “My Girl” and giving roses to girls. Only the hottest girls got them. Like, you could judge hotness based on roses. Anyway, after enduring this every year from seventh to tenth grade, I’d had enough. I was like Jennifer Lopez in Enough. I wanted to get a fucking singing telegram. I decided to buy an anonymous one for myself. I filled out a form and paid $3.
But when V-Day came, the singing seniors never came to my AP U.S. History class! So I went up to one of the senior hotties and explained that I wanted my money back because my telegram hadn’t been delivered. Which I knew because I’d ordered it for myself? He was either too dumb or too polite to laugh at me outright. But yeah, thinking back, pretty embarrassing.
8. The Text-Message Breakup
We’d been seeing each other about six months, but the relationship was still nebulous — talking, hanging out, occasional booty calls, never making real plans. After six months of that, you start to get tired. Valentine’s Day came with zero mentions of going on a date, until maybe 5 p.m. that night when he texted to ask what I was doing. I was exhausted — I’d been wearing a really uncomfortable corset-and-garter contraption all day on the off-chance I saw him, and I was annoyed at him and the underwear both. I responded by asking not just what we were doing that night, but where this whole relationship was going. He acted bewildered: “I don’t know what you’re talking about! I’m trying to see you right now!” We ended up in a lengthy text-message fight, culminating in me telling him to forget it and delete my number.
A friend later suggested that perhaps he was trying to surprise me, but honestly? The chances of that are slim to none. All I know for sure is that texting is an anti-climactic way to break up with someone. It’s like screaming silently in public.
9. Mirror, Mirror
Once upon a time at a marijuana-fueled liberal-arts school, I was a video-arts student who had fallen hard for a guy who, after extensive wooing, broke my heart when he abruptly left school to deal with personal problems. In a terribly misguided attempt to feel closer to him, I booked a reservation at the vegan restaurant where he’d worked and we had met. I dressed up in red and pink and went on a Valentine’s Day date with a full-length mirror. I set up two cameras and, in a fully booked restaurant surrounded by couples, spent 90 minutes eating a romantic prix fixe dinner while talking to myself. But the lighting was terrible and the sound was muffled by the crowd, so after enduring this humiliation I had neither a boyfriend nor footage to show for it. But as I was leaving, some kind older gentleman tapped my shoulder and said, “I hope your date knows how lucky she is.”
10. The Cubby-Hole Creepster
I experienced love for the first time in the first grade. I was so enamored that I could stare at him for what felt like hours. (Which in reality was probably about 30 seconds, given first-grade attention spans, but I’m sure it was creepy anyway.) On Valentine’s Day I carried a ream of construction paper and a pair of scissors to his cubby hole and stood there, transfixed, as I cut dozens of construction-paper hearts, one after another, scrawling “I LOVE ALEX” across each one. I stood there, lost in my task, until his cubby was completely full and my teacher pulled me away for a one-on-one lecture about appropriate boundaries and paper waste. Sexual consent and recycling: two universal virtues.
11. Cupid Wears a Whipped-Cream Bikini
I’d been casually hooking up with two guys when Valentine’s Day arrived and figured I’d hear from neither on the holiday. Instead, in an act of complete Schadenfreude, I went to a bar with some friends to watch desperation play out. Against expectations, one of my hookups texted me late in the night. Clearly a booty call, but I told him I’d bring a Valentine’s gift and picked up a can of whipped cream on my way to his place.
I knocked on his door, brandishing the whipped cream as the door opened, and I found myself facing his best friend. We looked at each other silently for a moment, then burst out laughing. “I knew he was gonna text you,” the friend said. “He’s so wasted, I think he passed out already.”
Sure enough, he was passed out in his bedroom with his shoes on. Eventually the friend left, apologizing that I now had to take care of the drunk idiot. So I went into his room and got to work taking off his hefty, snow-soaked shoes. He groaned awake. “Just give me half an hour and I’ll be ready,” he said groggily.
“Oh honey,” I said, “we are so not doing anything tonight.”
“But I thought I was just a piece of meat,” he said.
“You’re an idiot,” I said. I fed him a glass of water, both of us laughing.
“I can’t believe this is how we’re spending Valentine’s Day,” he said, as if we’d had plans (or any kind of romantic relationship) in the first place. He was so dopey, I couldn’t help myself.
“This is just one night,” I said. “We’ll have thousands more. Now go back to sleep.” Then I joined him on the other side of the bed. I stopped hooking up with other guys after that. We stayed together for several months. Definitely a fun one.