People Explain How A Romantic Gesture Instantly Backfired On Them
Image by Jill Wellington from Pixabay

Chocolates, flowers, and love notes are overrated.

While it's the thought that counts, letting the object of your affection know how you feel about them requires more creative thought to make a lasting impression.

However, not everything goes according to plan.

Being witnesses to a sad proposal, having flowers rejected due to skepticism, and a painful attempt at a strip tease were just some examples of botched declarations of love when Redditor Nzui_254 asked:

"What romantic gesture did you try to make that instantly and horribly backfired on you?"
Sometimes, even Cupid's aim is off the mark.

The Crushed Secret Admirer

"Wrote a letter to a crush on Valentine's Day. Signed it as his Secret Admirer and left it in his locker. Watched him open it. Still reading, he starts to approach me. I tense up."

"He goes, 'Its402Am...look at's from Angeline. She wants to get back with me!'"

"No idea how the discussion of the letter went down but they totally got back together."


The Love Concussion

"Took a date to a club; tried to do the tilt back while I hold her back, I dropped her. Married 7 years now..."


What Happens When You Over-Share

"Came to my wife for a hug...started out with an awww that's so sweet. Then I made the mistake of over sharing that I had asked one kid to watch a movie and another to play a game and no one wanted to do anything. Then she pipes up, oh so I'm third?! Fuuuuuuuuuuuuu*k."


Sad Witnesses

"I surprised my wife on Valentine's Day with a dinner at one of my wife's favorite restaurants that's really hard to get into. It was a crazy expensive three course dinner and the food was amazing. However... we got seated in a corner of the restaurant with our table and one other table that was about two feet away. We we were seated about the same time as the couple next to us. After about 5 minutes the guy gets down on one knee and my wife and I being 2 feet away are basically front row and start to clap... but the girl bursts into tears and says no. They then proceeded to eat dinner for the next hour, both crying the whole time. My wife and I pretty much ate our meal in awkward silence and couldn't really leave as we had to wait for each course."


Wrong Window

"My SO and I had a fight in college. So to apologize, the next day, I printed out a bunch of cute/funny memes and taped them to his dorm window."

"I texted him, told him to look out his window. 'Why?'"

"It was the wrong window. I was tampering with a strangers window. And probably freaked them the f'ck out. When I explained to my SO my f'ck up and we hurriedly went to take them off the window, the blinds were open lmao."


Mocking Chivalry

"In a thunderstorm I offered the girl I was on a date with my rain jacket (as a true gentleman should); we then both ran to her car. When we got there she was totally dry (fantastic rain jacket) and I was dripping wet from head to toe."

"She laughed at me for being so stupid as to give my rain jacket away. We broke up because she thought I was so dumb."

"Suppose I did dodge a bullet there."


No More Flowers Just Because

"Randomly bought my wife flowers. Big mistake. First thing she said was what had I done wrong, if I was buying her flowers, I must have done something wrong. No amount of having done nothing wrong could convince her. Oh, well lesson learned."


It Didn't Go Down Well

"I took my Ex to a pub (yes im british) and we were going to have a lovely pub lunch."

"she ordered the chicken in white wine sauce, i had the lamb... the lamb was raw and the chicken in white wine sauce hadn't been cooked properly so it was basically raw chicken and alcohol in a bowl."

"i complained and got a refund with the guy behind the bar saying 'yeah, its the cheifs last day and he was being let go' and followed on with 'his mate behind the bar over heard the conversation and told him before the shift, we have been handing out refunds left and right'"

"so i dropped my Ex off at hers and had to speed all the way home for what is commonly known as a 'photo finish' to get my a** on the toilet before all holy hell fell out of my god forsaken hoop, so head in sink vomiting and my arse leaking like a sieve, needless to say my grand romantic gesture lead to 2 people having the worst food poisoning of the young adult lives... the place closed down almost over night and i believe is under new management now."


The Note

"Spontaneously bought flowers to be delivered to my new wife while I was at work. When I got home she was fuming and had obviously been crying. Instead of a hug like I had been picturing all day, she greeted me by throwing a handful of ashtray smelling greens and stomping out of the room between half packed moving boxes."

"Turns out the driver had smoked cigarettes on the way over and besides the smoke smell there were some ashes on the bouquet. More awful though, I had asked that the note say 'I'm happy for the wonderful time we've known each other.' The note actually said 'It's been nice knowing you.'"


Love-struck Teen

"I wrote a poem for a girl when I was in high school at a summer camp (it was like a 4 week camp and idk what I was thinking honestly - lovestruck teenager). Her room was below and adjacent to mine and and my neighbor (directly above her room) happened to be somebody she talked to about things (like a brother relationship, he had a girlfriend at the time) and she decided to talk to my neighbor about the poem I gave her (they basically opened their windowsand talked up and down to each other). I overheard the entire conversation, and she pretty much thought I was a good guy but made it clear she wasn't interested at all like that with anybody right now. She pretty much stopped talking to me after that, didn't even explain herself, just avoided me. I probably would have been more hurt if I hadn't heard the conversation though honestly. The neighbor was a great guy, good friend about it with me though. She and another guy were pretty much making out though by the end of the week. I think it gave her the courage to make up her mind about things."


Strip Tease Fail

"Tried to do a strip tease for my boyfriend. Stepped fully on his foot in heels, and kicked him fully across the face as a grand finale. I was so mortified that I cried. He was a jerk though, so in the long run, 10/10 would do again."


Cat's Meow

​It wasn't a romantic gesture in my case. My girlfriend was upset that her cat died. So, I tried to cheer her up by making her laugh. She had this rubber popper thing. I put it on my forehead and got it stuck. Suuuppppeer stuck. Eventually, I pulled it off. Her laughing face turned to shock when she saw that the popper created a huge purple bruise right in the middle of my forehead. I had to go to work and high school with this huge purple splotch on my head for weeks. It did make her forget about her cat for a few minutes though.



Grand public or some rom-com movie-style gesture. I got broken up with after pulling one of those in college with my bf. As i grew older, I realized the negative implications of such overly romantic actions.

Though I'll admit, I do secretly hope to find at least one affectionate partner in the future.


People frequently confuse "grand" and "public" with stuff like this. "Grand" doesn't mean a proclamation on high about your undying love. "Grand" means something that is extremely meaningful.

I read about a guy who met his S/O someplace with bolts (can't remember exactly what. Maybe they were both working on cars or something at the time?) and so when he decided to propose he had a jeweler take a hex nut and turn it into a pair of rings. That is grand, IMO. Something that demonstrated an actual, substantial connection.



Spent $100 on a toy train set to put around the tree for Christmas, since my wife's talked about how there used to be one at her long-deceased grandpa's house.

Me, being dense as a rock, thought she missed the train.

Nope, she misses her grandpa, and she just so happened to see him mostly on Christmas, where he had the train set up.



How I Met Your Mother Comedy GIF by LaffGiphy

The Naked Man. no story needed. most likely the worst possible thing that could happen happened.


So it's true: 2 out of 3.


As a present for my then-boyfriend (now husband) for a significant event, I cooked all day and made lobster thermidor then chartered a night blue fishing trip. In our excitement, we both forgot he gets seasick if he loses the horizon.

Sun went down and he spent all 4 hours of trip chumming lobster into the ocean.

I didn't catch a bluefish.


Labor pains

Made this huge plan to do all these things while my ex was giving birth to our son to keep her relaxed and keep things calm and smooth.

Did literally none of it. Stood there like an idiot in a total stupor, while she was like: "Hey, you gonna be ok?"

The nurse was even like: "If you're going to pass out just go, because we aren't going to be stepping over you."



Tried to arrange a surprise party. If you're going to do this, don't do it by pretending your forgot her birthday.


Taking a stand

My husband had been working long hours, so I thought I would surprise him by putting together our new tv stand on my own.

I have never built anything by myself. I am terrible at interpreting directions for constructing things. But I had some really misplaced confidence in my abilities. Idk if I thought love and good intentions would guide me or some BS.

He got home late at night, and there were pieces of tv stand all through the living room. I was close to tears, had blisters on my hands, and was aggressively trying to get a screw to tighten that wouldn't budge. I didn't realize that I had stripped it. Our dog and cat could barely find any place to sit in the living room because of the mess I had made.

My husband was so upset and exasperated. He sat on the floor and had to finish putting it together. Kept asking me why I would do this when I know I'm not good at this stuff. Told him I was trying to do something nice and romantic. Lmao he was up for a while after that trying to fix my mistakes.

Ended up just making his night harder, so definitely not my best idea.


I would have appreciated the effort