10 Hilarious Stories Of “The Worst But Well-Intended” Romantic Gestures!

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Ah, love—sometimes it leads to unforgettable romantic gestures that, well, don’t quite hit the mark. In our quest for affection, we’ve all experienced those moments when our significant others’ well-intended gestures left us laughing, scratching our heads, or even blushing with embarrassment. As we delve into this collection of tales from the world of heartfelt but slightly misguided romance, you’ll see that even the most loving partners can stumble when trying to create the perfect moment.

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#1 When Good Intentions Meet a Stinky Surprise

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“We’re out walking our dog and strolled past some flowers. He picked one and tried to place it behind my ear… The problem was he was also holding a bag of dog poop that was hitting against my face while he tried.”

In the world of romantic mishaps, this comment takes the cake. Picture this: a lovely walk with your significant other, a flower gesture that goes hilariously wrong, and a bag of dog poop, adding an unexpected twist. It’s a perfect example of how even the best intentions can result in side-splitting, unforgettable moments.

#2 Practical Romance: Oil Change Edition

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“My husband is such a goof. Sweet but not what I’d call romantic. He’s very practical so instead of giving me Valentine’s Day presents or flowers every year, he gets the oil changed in my car and leaves a note with a Valentine’s theme that says “oil is changed…love you.” First few years, I was like seriously…now I swoon since I don’t have to deal with the oil change place.”

Who knew that a simple oil change could become the epitome of practical romance? This commenter’s husband found a way to make Valentine’s Day memorable without the usual gifts and flowers. It’s a prime example of how love can be expressed in the most unexpected ways, leaving us swooning for something as mundane as a well-maintained car.

#3 A Bloody Valentine

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“My first boyfriend gave me a wooden box with a padlock on it for Christmas one year, handed me the key and told me not to open it until I got home. I opened it and inside was a little jar of his blood, and a little jar of his tears. I was 17 and mortified. Also, couldn’t fathom how he got enough tears to fill a small jar, so I asked him. Turns out he’d plucked all his nose hairs and eyelashes to gather them.”

When it comes to romantic gestures, there’s a fine line between sweet and cringe-worthy. In this case, the line was definitely crossed. The wooden box and mysterious contents may have been well-intentioned, but the outcome was nothing short of mortifying, especially when the truth about those tears came to light.

#4 Freezing Romance at Rockefeller Center

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“My ex-boyfriend surprised me and took me ice skating at Rockefeller Center for Christmas once. It was a really sweet idea, but he had said we were going to a show so I was not dressed warmly at all. I was wearing a dress, tights, and a lighter but formal jacket, with no hat, gloves, or scarf. I was so cold after we had been on the ice for about twenty minutes that my lips turned blue and we had to leave. The thought behind it was really cute, but it would have gone so much better if I had been dressed appropriately.”

Ice skating at Christmas is the stuff of romantic dreams, but not when you’re dressed for a Broadway show. This user’s ex-boyfriend had a sweet surprise in mind, but the lack of proper attire turned their chilly adventure into a comedy of frozen proportions.

#5 A Sizeable Gesture, but the Wrong Size

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“In the beginning of our relationship, he went on a trip to Rome with his family. He brought back some shoes for me, a 6’1 woman. He was so excited when he handed over those (pretty nice) size 6 slippers. It was hard to break to him that I loved them, and I loved the gesture – but I am a giant and a size 10.5.”

The sentiment was lovely, but the practicality was a tad off, making it a humorous memory to cherish.

#6 When Poetry Spells Breakup

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“He gave me milk + honey by Rupi Kaur and underlined the parts that applied to our relationship. Including the parts about how f****d up and unhealthy it was, and how we knew we needed to break up. For my birthday. He was confused when my reaction was just a lot of crying.”

Poetry can be a powerful tool for expressing love, but it can also reveal uncomfortable truths. This commenter’s partner tried to convey their feelings through a book, but it backfired when the highlighted passages hinted at a less-than-healthy relationship. Sometimes, heartfelt gestures can lead to unexpected emotions.

#7 The Christmas Coat Mix-Up

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“A lot of these remind me of a story my friend told me about her first Christmas as an engaged couple living together. She wanted a new winter coat for Christmas, like that’s all she wanted. They were out shopping and she found one she liked on sale and told him to get it and wrap it and be done with it. He was like.. no I don’t want you to see me buying it, that ruins the fun, plus I bet I can find a better deal. Christmas comes and she opens her gift. It’s a coat! Except… it’s her old one. He tells her to look in the pocket, she’s thinking maybe it’s the receipt for a new one that’s being shipped. Nope. $100. He’s all excited that she can pick out exactly what she wants now.”

In this Christmas tale, the boyfriend actually seems to have forgotten to buy the new coat despite reminders from his girlfriend. His attempt to pass off the old coat with $100 as a romantic gesture becomes an amusing yet endearing attempt to make amends for his oversight. While it may not have been the most well-executed plan, it certainly reflects his desire to please his girlfriend and salvage the situation with a touch of humor and care.

#8 Tattoos of Love Gone By

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“My ex got my initials tattooed over his heart. He surprised me with it – I pretended to be flattered. We broke up a year later. I wonder if he still has that tattoo…..”

Tattoos are often seen as permanent declarations of love, but relationships sometimes aren’t. This commenter’s ex-boyfriend made a bold gesture with the initials tattoo, but it serves as a reminder that love stories don’t always have fairy tale endings.

#9 Sock It to Me

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“My boyfriend is an auto mechanic and he orders from snap-on a lot. He was super excited because he ordered me something from snap on for me. Hyped it up so much, I was excited, it took a few months to arrive. It was 6 pairs of pink thick work socks. I started laughing because I thought it was hilarious and sweet. I was expecting like a flashlight or some cool tool for my car. Just some socks he thought I would like.”

Gift expectations don’t always align with reality, as this user discovered. While they anticipated a tool-related gift, their boyfriend surprised them with pink work socks. The humorous and sweet reaction shows that sometimes, it’s the thought behind the gift that counts, no matter how unexpected.

#10 A Pajama Set Mishap

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“My husband got me some pajamas for our first Christmas as a married couple from Victoria’s Secret. One of the pajama sets had a shirt that said “single all the way” I was like eerrrmmm?”

This commenter’s husband’s mix-up is a perfect example of how even the most well-intended gifts can turn into comedy.

Source: Reddit.

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Hasthi Wand

Hasthi is a writer with nearly a decade of experience in editing, proofreading, and creating content on a variety of topics, including language, literature, travel, food, digital marketing, health, and wellness. In her free time, she enjoys reading novels, watching movies, and exploring new places.