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15 people share their romantic gestures that totally backfired.

15 people share their romantic gestures that totally backfired.


Okay, who doesn't love a good ol' grand romantic gesture? I mean, besides those of us who avoid drawing attention to ourselves at all costs.

Ross, this could have been done over the phone.
Ross, this could have been done over the phone.

These 15 Redditors shared their stories of attempted grand romantic gestures gone horribly, hilariously wrong. So if you were thinking of holding up a radio outside your crush's home or something...maybe you should just settle for a nice card instead.


1. The_Iron_Zeppelin is better off single.

I worked with this girl at a Ruby Tuesdays and for her birthday we all went out for drinks. We were all friends and I think she knew I liked her at the time though I hadn’t made move yet. She put off this rocker vibe, tattoos, colored hair, loved 80s hair metal and rock music in general. So for her birthday I decided to burn her a C.D of all of my favorite songs from the band The Kills, because lead singer Alison Mosshart kinda reminded me of her and I thought that their music would be right up her ally. So I burned the C.D on my computer, decorated the C.D cover with sharpie, made it look really cool. I wrapped it up with fancy wrapping paper and a bow and gave it to her at the end of the night.

I didn’t wait for her to unwrap it, partly because I was still nervous about her reaction to my gesture and partly because I didn’t want to put her on the spot while we were out amongst friends. I figured she would just let me know if she liked it at work the following week and I would use that as an opportunity to ask her out. Cut to next week, there was a day that I was off and she was working and so was a close buddy of mine from high school.

I come in the following day for work and he pulls me aside and says, dude you should just forget about her. He goes on to tell me she had basically shit talked my gift saying: “I can’t believe he did that, I don’t even like the Kills.” My friend and I are really tight and he’s very outspoken and defends me saying: “Are you kidding me? You should be so fucking lucky that anyone gives a shit about your birthday at all.”

When I heard about that incident it killed any interest I had in her. She never even thanked me for the C.D at all, she just never mentioned it and I moved on.

2. Im_JustinTyler's story has a happy ending.

I once had a car break down at the very beginning of my relationship with the girl of my dreams, however me being underage couldn't rent a car. But I could... Rent a U-Haul. For just 20 dollars a day and but 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. Alot. 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.


3. ASlap_'s kind gesture almost went up in flames.

My girlfriend at the time had this friend who passed away so I went out and bought chinese sky lanterns (little hot air balloons, pretty much). We wrote messages to her friend on them and launched them in the sky from my backyard. Hers careened right into a tree and almost set the whole damn thing ablaze.

4. JLisTheTruth was not feelin' the love in the most romantic city in the world.

I took my ex to Paris. Had the whole weekend planed. We went to the Eiffel Tower at night, had a picnic, basically did it all. She dumped me 2 weeks later. She said I "wasn't romantic enough" and didn't tell her I loved her enough when we were in Paris. OK.

5. loyaltangie lost a part of him when he divorced his wife.

I gave my now ex wife a kidney....


6. n4g4rok's dress did not impress.

Had 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.

7. AlexDawdy accidently set up his crush with her husband.

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.


8. ccasella3 accidently offended their girlfriend.

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.

9. TheNote7's surprise went unnoticed.

I 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. WELP

10. SomehowStillAwake's grand romantic gesture crashed and burned.

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


11. CITIZENFOUR's joke backfired. Hard.

Literally whispered the words "sweet nothings" into my new girlfriends ear.

(Whispering sweet nothings is a saying or general term used to describe a set of compliments or words intended to flatter or woo a lady)

This was my attempt to be sexy/romantic in a humorous sense. At the very least, I thought she would find it funny.

I thought wrong however... I was unaware that this was something her Ex used to say/do on the regular, so I'd did not come off sexy or romantic, but actually repulsed her since I reminded her of him at that moment.

12. A ride on a horse-drawn carriage sounds romantic. According to The_Town_Of_Canada, it's not.

Oh 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 give a shit 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.

You know what's more fun that a ride on a one horse open sleigh?

Drinking inside in front of a fireplace. Or anything. Anything is more fun.

13. ikkyu666's childhood crush crushed his heart.

Walking around at recess with my life-or-death crush Christina in 5th grade. I'd been planning this moment for weeks.

She was a small girl. I told her she reminded me of strawberry shortcake. She asked why and I responded "because you're short and sweet". She did not respond and I'm still dead inside.


14. LousyMinibus really showed their ass trying to impress a boy.

In 8th grade, I tried to hop over a little mini fence by the PE area to impress the boy I liked, needless to say I did not make it, and instead ripped the whole back of my pants, exposing my prepubescent ass to my fellow peers, well also falling forward and smacking my face into the concrete below the fence. Needless to say when the boy expressed his disinterest about me to his friends, I was not surprised.

15. DumpsterKraken's date-gone-wrong had the best possible outcome.

Decided to make a bold move with a close lady friend. Invited her over for a home cooked meal on valentine's day in my shitty college apartment since neither of us were seeing anyone (pretty smooth right? I thought so).

So I cook a pork loin and some pasta something or other, anddd purchased an expensive $12 bottle of wine. "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.

All's well that ends well, right?
All's well that ends well, right?
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