10+ People Who Tried to Be Romantic, but It Backfired

In their quest for love, many folks have planned heartfelt and thoughtful surprises, only to see their romantic attempts go in unexpected directions. From innocent mistakes to huge letdowns, some of these gestures made or broke relationships. Despite the outcome, some decided to share their romantic fails online.

After the date I dropped her off in the parking lot where her car was parked, we said goodbye and no kiss, it was our first date. She got out and began walking across the parking lot and I suddenly got the courage to whip my car around, stop right in front of her, get out, and kiss her.
In my head, it was like something out of a film. In person, I pulled up to her, forgot to put it in park, got out, walked away from the car, she looked at me horrified and pointed; I turned around and ran towards my car as it slammed into another parked car. Just a typical day in my life, really. © Unknown user / RedditI once had a car break down at the very beginning of my relationship with the girl of my dreams, however I couldn’t rent a car because I was underage. But I could rent a U-Haul. For just 20 dollars a day and a few dollars for extra mileage, I rented a U-Haul and was on my way to her house to pick her up for what promised to be the most awkward date of her life.
Until I pulled up, that is. For you see once I arrived I saw her family moving boxes from storage, and they had a lot of stuff. Like a lot. And they saw me pull up in a U-Haul and thought I was just the greatest help. So I instead had to help them all day with boxes. No date for me.
BUT We’re engaged now, so yeah. © Im_Justintyler / RedditTo celebrate our fifth Valentine’s Day together, I was going to replicate our first meal together over candlelight. It was Banquet chicken patties with marinara sauce and mozzarella melted on top, with pasta and a Dole bag salad. In the days leading up to it, when she asked what I was going to do, I told her I’d make a special meal. She laughed and said, “Probably just make the same food we did years ago or something dumb.” So, needless to say, I went to plan B.
But for the record, my wife is a very sweet lady. She was laughing about me being predictable, and not just being mean. © lotus38 / Reddit

I got painting lessons for a girlfriend because she was getting into painting. She took it to mean that I thought her painting sucked. She never took the lessons and I never got my money back. © ccasella3 / RedditOh what fun it is to ride in a one horse open sleigh!
Spoiler: Not fun at all.
I booked a weekend at a nice resort up north after the first decent snowfall of the year, and one of the options was a sleigh ride. I thought it would be like a Hallmark card. Couldn’t have been more wrong.
First of all, it’s way below freezing, but we were dressed for it. The horse had constant gas for the duration of the trip. Also, that horse doesn’t care that we’re there. He’s clipping trees, farting, hitting rocks, all in a sleigh with no suspension whatsoever.
“Hold on, this is where it usually tips over,” our guide says. As if bouncing around on solid wood behind a fart machine wasn’t bad enough, now it’s apparent that we can just fall over any time. It’s not that uncommon, though I’ve never seen it on a Hallmark card.
We came back cold, tired, and in pain. So you know what’s more fun than a ride on a one horse open sleigh? Having a drink inside in front of a fireplace. Or anything. Anything is more fun. © The_Town_of_Canada / RedditI emptied my wardrobe cabinet, and filled the cabinet portion of it and placed on the shelf flowers, chocolate, a stuffed bear and numerous candy that she loved. When I told her to get my “hoodie” out of the cabinet, she opened it and said, “it’s not here” and then proceeded to close the cabinet. © TheNote7 / Reddit

Valentine’s Day. My girlfriend at the time had been in Thailand doing yoga trainer certification. I managed to get in touch with the hotel she was staying in, and arrange for a dozen roses to be delivered to the hotel, which they would place in her room during clean up while she was at class.
On Valentine’s Day, she came home to roses and a knock on her door. I had flown from New York to Bangkok, and from Bangkok to Samui to surprise her. I got the bigger surprise, though.
Two days later I found out she had been sleeping with her ex who lived on Samui. I took a ferry to the next island over and had a two-week vacation by myself. © Unknown user / RedditDecided to make a bold move with a close lady friend. Invited her over for a home cooked meal on Valentine’s Day in my awful college apartment, since neither of us were seeing anyone (pretty smooth, right? I thought so).
So I cook a pork loin and some pasta, and purchased an expensive $12 drink. “She’ll be here any minute,” I kept telling myself. At around 9PM, I texted her. She let me know that she assumed the invite was a joke.
She did eventually sheepishly show up! We are now married, and I remind her of this every Valentine’s Day. © dumpsterKraken / RedditMy ex and I were to get married in 18 days, and we were really stressed out about the wedding. So I left work early, got a bunch of things, cooked dinner, set up a little scavenger hunt of memories to remind her of why we’re together, which then lead her to the dinner table with her favorite meal with candles.
She then broke up with me, lied about why she did it. And I found out a few weeks later that the reason we were having trouble was not wedding related. It was because she was with someone else. © throwyoworkaway / Reddit

Sophomore year of high school, there was a girl I really wanted to take to homecoming. I decided I would do a scavenger hunt and at the end if she found me I would ask her to homecoming with flowers. We were friends, and she already knew I liked her, and she had said she liked me as well. She completes the scavenger hunt and finds me, I give her the flowers, she says yes. I was so excited.
Fast-forward to the night of homecoming. I go to pick her up from her house. Knock on the door, her mother answers and asks who I am. I tell her that I am her daughter’s date for homecoming, she then proceeds to tell me that her daughter left 15 minutes earlier with a different guy and said if I show up to tell me that the scavenger hunt was “a little excessive.”
So instead of her just saying no right away, she waited until I showed up to her house and had her mom tell me. I was so embarrassed. Never attempted to attend another school dance after that. © Nerdyhusband88 / RedditHad a girlfriend come live with me after being in a not so great situation for nearly a year in another state. Was planning for 8 months to have a dress she had been dying to get waiting for her under the Christmas tree when she arrived because she hadn’t had the cash for groceries, let alone a nice dress. So, she got super excited when she saw the box and opened it right away. I bought the wrong dress.
She appreciated the effort though and wore it for fancy events. I ended up getting her the correct dress for her birthday a while later. Now we laugh about it. © N4g4rok / RedditI made a huge plan to ask my crush to prom. Made signs to her house asking her but didn’t put up a name saying who did it. Well, turns out her neighbor had a crush too and took credit for it. She said yes to him. Nobody believed I did it, and they’re now married. © AlexDawdy / Reddit

Being in a relationship is tough, and often it means having to make sacrifices for the one you love. For some people, those come in the shape of secrets they keep just to spare their partner’s feelings. Still, that doesn’t stop them from sharing them online anonymously.

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