So, when a Reddit user asked, 'what's your worst attempt at a romantic gesture?' people were ready to confess their most humiliating moves, poorly executed choices, or overall failures in the art of romance. R.I.P., public proposals with flash mobs and hiding diamonds inside of edible items.
We were getting in the mood for sex and she says 'I'll take you where only dreams can.' Might sound good for most guys but I found it so incredibly cheesy so I burst out laughing. I slept in the guest bed that night. - whatever_idc
In eighth grade, I liked a girl. We were goofing around before class started, fiddling with some lab equipment. I was waving a wooden yardstick around, and I naturally felt that I should impress this girl with my samurai-like physical mastery of the yardstick.
I told her to sit still at her desk, and she smiled and obliged. I held the heavy wooden yardstick like a sword and rested its blade lightly against the crown of her head. A few classmates stopped talking to watch.
In a grand gesture, I raised the yardstick high in the air, grinned, and brought it slicing down at her, only to stop it rigidly a daring half-inch from her lovely head.
Or that's what should have happened.
Instead, overcome with adrenaline and bravado, I brought it solidly and swiftly down, with full follow-through, and cracked her brutally over the head with all my strength.
The class gasped. The yardstick clattered to the floor.
The girl's face – which held an innocent, curious smile a moment ago – twisted in pain. She turned away from me, laid her head on her desk, and began sobbing quietly. I, burning with incredible shame, sat down in my seat without a word. The girl and I never spoke to each other again. - utterpedant
Decided to bake my diabetic ex-girlfriend strawberry cupcakes for Valentine's Day. She had told me many times before she didn't like strawberry. - IHate90sBands
For my first valentine's day with my girlfriend we were going to two different colleges (me in Illinois and her in Minnesota). She was sad that we were going to be apart but I had decided I was going to get there somehow to surprise her. I just told her I was sending her something in the mail for v-day. the night before v-day I took a 3 hour shuttle back home and the next day I caught a 5 hour train ride up there and got picked up by one of her house mates.
By then it was already night but my gf was out at some type of performance so I had time to set up her room with candles and a teddy bear on her bed and leave her 'mailed' present on the kitchen table. The plan was for her housemate to tell my gf that she had gotten a delivery while she was gone and for my gf to open the package to find some crappy chocolates and a poorly written letter to make her think I half-as*ed her gift, but then the note would tell her there was a surprise waiting in her room.
Unfortunately when she returned home and was told of her gift by the house mate she decided she wanted to go to her room first to put away her coat. Hearing this and not being ready, I for some reason rid in her closet. My gf comes into her dark room, sees some candles lit and looks confused.
I figure hiding in the closet is stupid so I start to come out as she turns and sees a dark shadowy figure coming out of her closet. She screams and almost takes a swing at me, but luckily my voice yelling in surprise stopped her. - BarkingTurnip
I was saving to buy an engagement ring for my wife (then girlfriend)... she got pregnant and I decided to buy a ring even though I hadn't reached a level to buy the ring I wanted for her. I wanted her to know that I already had this in the works before she got pregnant. I wanted to propose in a romantic way, but the clock was ticking...I got antsy and proposed to her in our bedroom as she got out of the shower...fail.
I made myself a resolution that I would start saving and buy the ring that she deserved and I would give her the proposal she deserved. 8 years and $7,600.00 later we decide to have child #2. I plan to buy the ring, reaffirm my love for her, and re-propose in the hospital shortly after our child is born.
I buy the ring. I get excited and antsy again..... due date is two months away....I propose on the couch while we're watching TV. Double fail. She was happy both times, but it would have been so much better if I had a little restraint and done it the way I wanted. - B0h1c4
When I was a stupid young man, I had a crush on my friend's sister. She was beautiful, smart, funny, etc. So I decided to make a gesture and get her some flowers, a dozen or so. They were from a fundraiser some school club was doing, so they would be delivered to her during class.
Apparently, the flowers were less 'romantic' and more 'embarrassing,' because she stopped talking to me completely. Completely completely. To this day she will not speak to me. - dkydi
Sophomore year of college, I was dating a guy long distance. We decided to make each other Christmas presents because I was dead broke. I got together a bunch of cardboard boxes from when I moved and shlepped them to his apartment on the train- instant box fort! So many good times and video games to be played and sex to be had in the box fort! He hated it. We never made the fort. - malprintemps
Her: I forgot to shower today
Me: I showered today... For you
Her: Aww - Halpert
For my boyfriend's birthday I adopted a barn owl in his name. I chose the 'female owl' option, and signed it 'From the new girl in your life'. When the certificate and photo arrived it began with 'This is to certify that 'Boyfriend' has adopted 'name of his ex-girlfriend'. We estimate her hatching date to be 'exact date of his ex-girlfriend's birthday.' I adopted my boyfriend's ex-girlfriend for him for his birthday. - LadyWhiteadder
I was 16 at the time, so this isn't as cheapskate-ish as it sounds: Went to the cinema before a meal with my, now ex-girlfriend, on Valentine's Day. We saw Cloverfield.
She literally sh*t herself at the end when they're under the bridge and a bomb goes off or something, I don't remember the exact story, there were more hilarious matters occuring.
Upon leaving the cinema and telling me what happened, she exclaimed 'Eurgh, you've farted! That stinks!' and proceeded to perform some strange combination of running and waddling to the far side of the car park to phone her Dad to pick her up. - Econogeek
Delivering a birthday cake I spent 4 hours making to my gf when I was 15 going up and down over hills on my bicycle over 6 miles. It was just mush by the time I got there, and she cried. that was all I could afford at 15 for a present. Didn't last long after that. - judith_lies
Valentine's Day 2004 (I was 17): I found a beautiful field, pitched a tent, started a campfire. Got steaks cooking and everything was going swimmingly. Dusk came and I sat there with the girlfriend just kinda hanging out.
From up the hill I see a car pull up behind mine. I go investigate because the person is looking into my car with a flashlight. Turns out it's a cop. He draws his weapon on me and tells me to freeze. Frisks me, finds a condom and that's it. I request to see a badge - he doesn't show me.
Arrests me. Throws me in the back of the car. Calls gf's mom - tells her about the condoms and that we're trespassing on church property and someone called the cops. Not only did I get arrested. I didn't get laid. Good steaks went uneaten. And no one put out the f*cking fire. - Sniper1154
I made a path of rose petals and candles leading up to her bed where I made a heart shape using rose petals and strawberries on top of them. She ended up accidentally kicking the candles burning a small hole in the carpet. Then, when she sat down on the bed, the strawberries rolled off the petals staining the bed sheets. - Nothingtocontribute
Boyfriend and I had been together for a mere week or so. Smitten, we decided to take a romantic bubble bath together. Cut to bubble bath, we're kissing and he decides to turn on the jets.
We continue kissing for a few seconds before he looks down and emits a strangled cry of horror and scrambles to escape from the tub. Hundreds of dead cockroaches/cockroach body parts are swirling around us.
When we got out we were covered in antenna, legs, wings and other bits of roach bodies. Turns out the tub was in the guest bathroom and hadn't been used in a couple of years and a colony of roaches had taken up in the pipes of the jets, their bodies gradually building up over time before being flushed directly into the midst of our would-be romantic bath time moment. Let's just say that neither of us were in the mood after that. - kapac
I bought roses for this girl I liked for her birthday when I was a kid. Problem was she didn't like me. I summoned enough courage to walk up to her door. I was sure she was home, but her brother opened the door, said she wasn't home, took the flowers inside and shut the door. She never mentioned it to me, or talked to me ever again. oh, one more thing. We were neighbors... - rothwick
I decided to be cute, and ask a girl out using a stuffed animal. The stuffed animal, in this case a bear, had a note around it's neck saying 'I'm bear-y serious that I want you to be my girlfriend.' I set it up in my car when she went to go get coffee, so when she opened the door, ta-da! romance happens.
She gets back, opens up the door sees the bear, lets out this shriek, drops the coffees, which hit the ground, explode, get on the seat and her clothes, and she breaks into tears.
Apparently, she had a bad run in with a bear as a kid, and was terrified of all bears, regardless of how cute they are in stuffed animal form. After throwing the bear away (only way she'd get in the car), buying new coffees (and eventually new pants), she said accepted my offer. - l33tb3rt
Planned to run a bath with candles and a special 'jelly bath' thing I bought for my g/f. She gets back a bit early and wonders quietly into the bathroom where I'm squatting next to the tub in nothing but my boxers, patiently watching the bath fill up while picking my nose with one hand and scratching my arse with the other...
All the while bathed in candlelight and humming along to a tune in my head. She was a bit miffed, stood there watching for a minute, and then asked what the hell I was doing - sgst