Stories of Grand Romantic Gestures Gone Horribly, Horribly Wrong

Valentines Day sucks, but these botched expressions of love suck worse.
February 14, 2019, 8:56pm
Photo by ICT_Photo via Getty Images

Whether you’re single, dating, or in a relationship, you can surely admit that Valentine’s Day is a trash holiday that we’ve all been nonconsensually conscripted into. If you're one of those who thinks they like the holiday, I'm sorry, but that’s just Stockholm syndrome talking.

As if the pressure and anxiety of this needless holiday wasn't bad enough, a lifetime of romcoms, CW shows, and other pop culture poisons have warped our collective expectations of romance. This disconnect between fiction and reality usually just results in unrealistic standards and unfair comparisons, but every so often it also deludes someone into believing the best way to woo their crush is with a recreation of the John Cusack boombox scene from Say Anything or something.

To help take some of the sting out of the holiday, we asked people to share their stories of romantic gestures that crashed and burned like the Hindenburg. Whether you’re overpaying for dinner and flowers tonight or wallowing in your own singledom, you can at least take solace in the fact that you’re doing better than these people.

As a teen, I snuck up to my girlfriend’s window in the middle of night unannounced, hoping to surprise her. She thought I was some kind of predator or rapist, so she sent her dad outside to check it out and he ran me down the whole goddamn street.
-Calvin, Grand Rapids, Michigan

We had only been together a couple months and things were kind of rocky. He had been away for the weekend and I was supposed to pick him up from his return flight. I had the brilliant idea to surprise him at the airport wearing five-inch heels and this terrible long over coat… and nothing underneath. I thought that would blow him away and reset things to get us back to a good place. I also used car paint to decorate my car windows saying, “Welcome home, Bozo!!” and “Welcome back, idiot!!” (Pet names, clearly). The whole drive to the airport I had a massive panic attack because I’d convinced myself I was going to get pulled over for something stupid and then get arrested for prostitution. I made it to the airport and I started to cry, because I was so uncomfortable physically and emotionally, so my makeup was running. On top of that, one button on my coat kept popping open. I realized there was no way I could be seen in public in my “get up,” so I called him to say I wasn’t coming in to greet him and he’d have to meet me out front. He got out to the car and kind of liked the decorations but was also sort of annoyed and super tired and low-key buzzed from drinking on the flight. He saw what I was wearing and instead of being PUMPED, he saw this crying girl in a terrible trash outfit. I started yelling at him for drinking on the plane and not appreciating “all I had done for him.” We fought the whole car ride to his house where we ultimately broke up in his driveway. I was so mad and sad, but mostly embarrassed as hell, so I went to my mom’s and slept until early morning when I had to get up a do event photography for my new job. In my emotional state and rush, I forgot to clean my car windows. For some reason, the owner of the company was at this event and I was such a hot mess and pulled up in my car with “Welcome back, idiot!” all over it. The owner had questions. I tried to make it sound funny, but was too sad girl and made it really awkward instead, so he didn’t know how to respond and everything was downhill from there. I was not asked to be part of any major event photography gigs after that. Funnily enough, we're still together. It’s been like five years.
-Rachel, Hershey, Pennsylvania


Spent two weeks making a girl (who knew I liked her) a Christmas card saying something to the effect of “I know you’ve grown so much since we met and I really care about you” and brought it to a party we were going to together. I told her I’d give her the card by the end of the night and she was hanging out draped around me all night. Then she got drunk and I walked in on her in a room making out with a dude who has a fiancé. We looked at each other and I walked out of the room without saying a word and wound up getting blocked on all her social media after saying nothing.
-Gary, Denver, Colorado I met a guy at a party and we hit it off. We hung out for a few weeks, made out, did some mouth stuff and hand stuff, but never went all the way because he didn’t have any condoms and wouldn’t fuck me without one. I thought it would be a hot gesture to take matters into my own hands. So, one night after work I bought a giant box of condoms, drove to his house, and left them in the mail drop of his front door with a note that read: “LET’S GET IT ON.” After leaving the package, I went down the street to a bar to meet my friends for a drink. Well, the guy just so happened to be there at the bar with another girl. I felt so dumb, and distanced myself across the bar to stay out of sight. After a while I noticed they had left the bar together. Knowing they most likely went back to his house, where they’d stumble upon a giant box of condoms and my note. Strangely, I never heard from him again.
-Cat, Phoenix, Arizona

Gave 11 years to someone and ended up tattooing her name on my face to show my devotion. She left less than a year after I got that done.
-Zach, Pismo Beach, California

It was our first Valentine's Day together and I wanted to do something exceptionally impressive. Now, keep in mind, I was not financially well-off at the time. In fact, I could barely make rent each month with the job I had, but this was a special occasion and I wanted to do something wild and memorable.


I rented a convertible Mustang, picked her up from work, and told her we were headed on a road trip. She was a bit perplexed but was always down for an adventure. Bags packed, we headed north for San Francisco where I had rented a sailboat on Airbnb for us to stay on for the weekend.

Things started to fall apart almost immediately. To kick things off, the drive up was completely rained out so the convertible stayed up. Then, as soon as we get there, the boat owner tells us that there's no way we can take it out (something they had said yes to prior to renting) because of the rain. Other plans we had made were also forced to be cancelled because of the weather.

So here we are, stuck in freezing SF on a boat that didn't have proper heating, like sitting ducks in a random harbor. We're both still trying to make the best of the situation while wrapped in layers of warmth. I remembered the bit of MDMA I had brought with me, so we gave that a shot. In a desperate attempt to find a quick resolution, we insufflated it rather than just swallowing it. We immediately added this to our list of mistakes as we realized the sharp crystal structures of the MDMA were unlike your average regular powdered recreationals. Goodbye nose, hello two hours of insufferable face pain.

As we're lying there, all but completely dejected, we look at each other and realize there's one more thing we can do to turn this night around. Things start heating up and we're both thinking FINALLY some pleasure to this crazy day. But the universe did not want to give it to us. The final kicker to this perilous Valentine's Day weekend? A sudden case of candida that stopped us dead in our tracks – the final blow before we completely signed off from the day and went to sleep.
-Noah, San Diego

Five-ish years ago, I gave my ex a breakfast sandwich maker for Valentine's Day. He told me it was useless, and then, two days later, he sent me a photo of it thrown in the trash. We broke up. He was a sociopath.
-Hilary, Los Angeles

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