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Well, That Backfired: Romantic Gestures Gone Horribly Wrong

Mathew Burke

Ah, romance. To some people out there, it seems to come as second nature. To the rest of us, though, it remains one of the greatest mysteries that we can ever hope to crack. Unfortunately, when one person likes another person and wants to somehow express that feeling to them, any gesture that is chosen could go seriously wrong. After all, what’s romantic to some might be creepy to others—or in some cases, maybe even a lot worse than that! Here are 50 stories about times when people’s romantic gestures completely backfired.


1. One Wild Ride

After a date, I dropped the girl off in the parking lot where her car was parked. We said goodbye to each other and parted ways without a kiss, as it was our first date. As she got out and began walking across the parking lot, I suddenly got the courage to whip my car around, stop it right in front of her, get out, and kiss her.

In my head, it was going to be like something out of a movie. In real life, I pulled up to her, forgot to put the car in park, got out, walked away from the car, watched her look at me in horror and point, turned around, and ran towards my car as it slammed into another parked car. Just a typical day in my life really…

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2. What Are You Trying to Tell Me?

One time, I wanted to do something romantic for my girlfriend. So, I decided to sign her up for painting lessons as a surprise present because I knew that she was getting into painting. She took the gift to mean that I thought her painting sucked. She never took the lessons, and I never got my money back either.

ccasella3

3. Dinner Is Served

To celebrate our fifth Valentine’s Day together, I was going to recreate our ever first meal together over candlelight. It was chicken patties with marinara sauce and mozzarella melted on top, along with pasta and a Dole bagged salad. In the days leading up to it, when she asked what I was going to do, I told her I was going to make a special meal. Her reaction broke my heart.

She laughed and said, “You’ll probably just make the same food we had years ago or something dumb like that.” Needless to say, I had to change to plan B. For the record, my wife is a very sweet lady. She was laughing about me being predictable, not just trying to be mean or hurt my feelings or anything like that.

lotus38

4. Unwanted Guests

I liked a girl in high school so I decided to throw a party and invite my entire class over in order to make her think I was cool. So, everyone came over and we were all having a great time. I thought my plan was going to work out perfectly. Then it all backfired when I walked into my guest room and saw the girl in question making out with a classmate…

hank_the_nightowl

5. Thinking Inside the Box

Every day, I wrote down one reason why I loved my girlfriend on a little piece of paper and put it into this box that I had. This went on for about a year and nine months. I was planning on saving them all for an anniversary gift or a proposal or something down the road; but instead, we had a nasty breakup and I just threw them all away. I never told her about it.

benfisher22

6. Missing the Point

I emptied all the clothes out of my wardrobe cabinet and filled the entire thing with flowers, chocolates, a stuffed bear, and numerous candies that my girlfriend loved. I wanted to surprise her with this stuff, so I asked her if she could go grab my hoodie out of the cabinet. I then patiently awaited her reaction to discovering the surprise.

Instead, she opened the door, said “It’s not here,” and then proceeded to close the cabinet without noticing any of the stuff I had prepared.

TheNote7

7. The Key to Her Heart

There was a girl in my high school who I really liked. One day, I happened to notice her locker combination as she was putting it in, so I thought it would be romantic if I opened it and left a surprise inside for her. So, I left a note with a rose and a poem on her top shelf. The next day, the principal called my parents and security took me to his office to ask why I was harassing the girl.

That was quite an embarrassing ordeal…

liamcurran115

8. Staying Hydrated

I had a huge crush on a guy that I used to see around the gym pretty often. I noticed he would go to the water fountain a lot, so I decided to buy him a Gatorade as a cute little romantic gesture. When I finally summoned up enough courage to give it to him, I walked over to him and said, “I hope you don’t think I’m weird, but I bought you a beverage.” He smiled and told me that it was, indeed, pretty weird.

That was not the response I had been expecting! I then walked away without looking back. I haven’t seen him back there since.

florida_grown

9. Poison Ivy

I once tried to be romantic by buying a bouquet of flowers for my girlfriend. As soon as I gave them to her, her mom took a look at them and said they were poisonous. Apparently, her mom was some kind of plant expert and knew how to spot the signs of poisonous flowers. My girlfriend is now convinced that I tried to kill her.

peterlalaland

10. Save the Last Dance for Me

I asked a girl to prom in high school earlier this year by putting her name and the word “Prom?” up on the scoreboard before baseball practice one afternoon. All the players on our school’s baseball team were there to witness it. Sadly, it backfired when she said no. I see her every single day, so it was awkward as heck around school for the next week or so.

OriginalFly7

11. A Bridge Over Troubled Water

I wanted to surprise my girlfriend by taking her on a romantic date to a bridge overlooking a river. I couldn’t believe how quickly it backfired. When she saw where we were, she informed me that this was the exact spot where her first-ever date with her awful ex had taken place.

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12. Under Pressure

I cooked a romantic Valentine’s Day dinner for an ex of mine back in 2002 or so. I was making some sort of chicken dish. I put it in a pot to cook. Meanwhile, my girl and I were hanging out in the bedroom while it was cooking. Let’s just say we got a little “preoccupied” for the next little while. Then, a few minutes later, I suddenly thought “Uh oh, the chicken!” and went running downstairs to check on it.

I ran into the kitchen completely naked and grabbed the lid off. Apparently, I had unknowingly used my roommate’s pressure cooker. I didn’t actually know what a pressure cooker was at the time, but I definitely do now! I forced the lid open and got boiling water all over my stomach, arms, and private area. I spent the rest of that Valentine’s Day in the emergency room getting burns treated.

drewuncc

13. The Calm Before the Storm

It was 18 days before our wedding and we were really stressed out about it. 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 were together in the first place, and then led her over to the dinner table with her favorite meal and candlelight ready and waiting.

She then broke up with me and made up some kind of bizarre excuses as to why she was doing it.  And I found out a few weeks later that the reason we were having trouble and stress in our relationship was not related to wedding planning. It was because she had been seeing someone else on the side. So much for that gesture!

throwyoworkaway

14. A Burning Passion

My girlfriend at the time had this friend who had passed away, which made her really upset. So, to try and cheer her up, I went out and bought some Chinese sky lanterns. We wrote messages to her friend on them and launched them up into the sky from my backyard. The plan backfired when her lantern immediately careened right into a tree and almost set the whole darn thing ablaze.

ASlap_

15. French Connection

When I was dating my ex, I once took her to Paris for a romantic weekend getaway. I had the whole weekend planned out perfectly and everything went smoothly when we were there. We went to the Eiffel Tower at night, had a picnic, and basically did it all. She then dumped me right when we got back. I was shocked and wanted to know why. Her reason was infuriating.

She said it was because I “wasn’t romantic enough” during our trip, and didn’t tell her I loved her enough times while sightseeing. Okay then…

JLisTheTruth

16. Strolling Through the Park One Day

I was walking around at recess with my life-or-death crush Christina in fifth grade. I had 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 we did not speak again after that day. I’m still dead inside.

ikkyu666

17. Say Yes to the Dress

I once had a girlfriend come to live with me after being in a not so great situation for nearly a year in another state. I had been planning for eight months to have a dress that she had been dying to buy waiting for her under the Christmas tree when she arrived. At that time, she didn’t have the cash for groceries, let alone a nice dress; so I knew she would appreciate the gesture.

When the big day finally arrived, she got super excited as soon as she saw the box and she opened it right away. Turns out I bought the wrong dress…

N4g4rok

18. Blast from the Past

My new girlfriend asked me to whisper sweet nothings in her ear, so I literally whispered the words “sweet nothings” into her ear. In case anyone doesn’t know, “sweet nothings” is a saying or general term used to describe a set of compliments or words intended to flatter or woo a lady. I knew that, of course, but this was my attempt to be sexy and romantic in a humorous sense.

At the very least, I thought she would find it funny. I thought wrong, however. As it turned out, I was unaware that this exact joke was something that her not so nice ex-boyfriend used to say and do on the regular. Because of that, I did not come off sexy or romantic, but instead, I actually repulsed her since I reminded her of him at that moment.

ClTlZENFOUR

19. Who Done It?

I made a huge plan to ask my crush out to prom. I made a bunch of very large signs and placed them outside of her house, asking her the big question. Unfortunately, I stupidly didn’t put a name on the signs saying who did it. Well, it turned out that her next-door neighbor had a crush on her too. He took full advantage of the situation and acted like he was the one who had put the signs up to ask her out. She said yes to him.

Nobody believed me when I tried to tell them that I had actually been the one behind it. Oh, and on top of that? They’re now married.

AlexDawdy

20. Haul Away

I wanted to pick up my new girlfriend for a romantic evening, but my car suddenly broke down. She was the girl of my dreams and I was very concerned that this would ruin our evening. Unfortunately, me being underage at the time, I couldn’t rent a car. However, I soon discovered that I could rent a U-Haul truck! It would cost just 20 dollars a day plus a few extra dollars for the mileage. What could go wrong, right?

So, 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. Once I arrived, I saw her family moving boxes from storage, and they had a lot of stuff. Like, a lot. As soon as they saw me pull up in that truck, they thought I was just the greatest help.

So, instead of the romantic evening I had planned, I had to spend the next few hours helping them move boxes. No date for me. But we’re engaged now, so I guess I can’t complain!

Im_Justintyler

21. Picture Perfect

I made a large portrait of my girlfriend. We had been fighting a lot and had not spoken in a few days, so I decided to do something that I thought would be romantic to win her back over. So, I drew a portrait based on my favorite photo of her. When I presented it to her, she got extremely mad and claimed that it made her look ugly. Gee, thanks!

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22. On the Fence

In eighth grade, I tried to hop over a little miniature fence by the gym area to impress the boy I liked. Needless to say, I did not make it, and instead ripped the whole back of my pants apart, exposing my prepubescent behind to my fellow peers. I also fell forward and smacked my face into the concrete below the fence.

Needless to say, when the boy expressed his lack of interest in me to his friends, I was not surprised.

LousyMinibus

23. Her Initial Reaction

At around the age of 15, I had a couple of my buddies help me write out mine and my crush’s initials inside a 20-foot heart, all made out of fallen autumn leaves. We then all watched as she sort of casually walked past it later and said nothing. She definitely saw it. The only word I can think of to describe that moment is awkward.

Sa3th

24. You Are What You Wear

For my entire high school career, I was goth. I was always wearing band tees and combat boots. I looked really grungy. It was just my style, and I liked it. Now, I happened to really like a guy who was friendly but didn’t seem interested in me, so I decided that a nice gesture would be to come to school one day dressed “pretty,” with pink lipstick, a skirt, and normal boots.

I thought for sure that he would see me as an ugly duckling turned swan. Sadly, that is not what happened. Everyone laughed at me the minute I walked in. I was teased all day about my makeup and the girls were all whispering about how dumb I looked for trying to dress like them. The guy I liked didn’t even take notice, and worst of all?

He started dating another girl in my class a few days later.

Fullmetalmedusa

25. Check Yes or No

In middle school, I wrote a love note to a guy in my class who I had a huge crush on, asking if he’d be my boyfriend. He was really friendly to me in the class we shared and always made it a point to talk to me, so I thought he liked me too. He was part of the cool group, though, and I guess I didn’t notice that he never spoke to me outside of class.

I walked up to him during our lunch break to give him the note. For some reason, my stupid kid brain decided that passing notes in class was against the rules, so clearly doing it at lunch in front of everyone we know would be better. His jerk of a friend snatched it out of my hand, opened it, and read it out loud to everyone at their table.

They all started to laugh hysterically at me. My crush looked mortified, which I guess counted as a rejection. He never sat anywhere near me again in class, which unfortunately meant that we never spoke again. I was subsequently picked on and made fun of every single day by his group for the next year and a half over this incident.

It was pretty terrible.

Wiffle_Snuff

26. Guess Who’s Coming to Dinner

I once decided to make a bold move with a close lady friend of mine. I invited her over for a home-cooked meal on Valentine’s Day at my lousy college apartment since neither of us were seeing anyone at the time. Pretty smooth move, right? I thought so. So, I cooked a pork loin and some pasta with something or other on the side.

I also purchased an expensive $12 bottle of wine. “She’ll be here any minute,” I kept telling myself as I waited. At around 9:00 in the evening, there was still no sign of her. I finally decided to text her. Her response made my blood run cold. She told me that she had assumed my invitation was just a joke. That’s definitely what you want to hear in that situation, right?

Believe it or not, she did eventually—albeit sheepishly—show up at my place once I explained that I had actually meant it. I think she was totally surprised and caught off guard. So, even though the initial romantic gesture backfired, the evening wasn’t a complete failure! We are now married, and I remind her of this story every Valentine’s Day.

dumpsterKraken

27. Poetic Injustice

I used to write my boyfriend one romantic sonnet per week about how much I loved him. After a while, this little activity got me to really enjoy writing to the point where I wanted to do it for a career. When I called to tell him that I had gotten accepted to the writing program at my university, he told me that he’d been seeing someone else for two years and that he hated my writing.

He then ripped up all of my poems on the phone for me to hear.

makeupyourworld

28. Mall-icious Intent

My college roommate once publicly proposed to his girlfriend in our local mall. The bad part was that he really went way too over the top, and that kind of freaked out his girlfriend who was quite meek. As they stood there with all eyes on them, she quietly whispered into his ear that she was not ready for marriage, and then went home.

Believe it or not, my buddy just shrugged it off. He didn’t seem phased by it at all. He knew that he wouldn’t see any of those people from the mall again; and that, if he did, they probably wouldn’t remember or recognize him. He was really level-headed about the situation. That was the weirdest part to me, to tell the truth…

KHDTX13

29. Your Song

I once gave my crush a little basket filled with two roses wrapped in poetry, enclosing tickets to Les Miserables. I handed it to her in the campus parking lot as we walked to the dorms. She was not impressed and thought that my poetry was creepy. Ever since then, I have abandoned all poetry and songwriting as a wooing technique.

Composing art about people sounds awesome in theory, but in practice it just makes you seem obsessed.

LeRoienJaune

30. Bookworm

I was once dating this girl and bought her a rare, out of print, hard to find book that she had mentioned wanting months earlier. It took like two months of following online marketplaces to find, and I was really excited to give it to her as a surprise. Unfortunately, she broke up with me before I could give it to her.

On the positive side, it turned out to be a really high-quality book that I ended up reading myself. I now proudly keep it displayed on my bookshelf. It’s not about a subject that I care about in particular, but it’s still a cool thing to have. It always reminds me of her a little bit every time I glance upon it, even though she doesn’t know about its existence.

matkalaukku

31. Raise a Little Hair

Right before my girlfriend and I were about to head out to a swimming pool, I shaved my chest hair in the form of her name. I thought I was being cute and romantic, and that she would definitely love it when she saw. Instead, I was forced to spend the entire afternoon by the poolside with a t-shirt on while she swam like a dolphin with her friends.

NewPony13

32. Making It Official

I was dating this girl who I was really into. I thought it would be romantic if I jumped the gun by sending her a surprise request to be “in a relationship” with me on Facebook. She then texted me telling me that she wasn’t ready for that kind of commitment yet. Boy, was I embarrassed when I next looked at my Facebook and saw tons of notifications that people had “liked” my update and asked who the lucky girl was.

Needless to say, we never went on another date and I learned my lesson about taking things slow.

WhatWouldTylerDo

33. On the Rocks

During my senior year of high school, I had a girlfriend who I had been going out with for a while. With graduation getting closer and closer and each of us having different plans for our futures, things between us were starting to get tense and our relationship was feeling pretty rocky. After enduring this situation for a while, I decided to do something romantic to smooth things over again. What a mistake.

There were these really tall cliffs over the lake in the town we lived in. Our first official date was there, and in the early days of our relationship, we spent a lot of dates at those cliffs. When things got rocky, we hadn’t gone to them in a while. I thought that heading over there with her would be a great way to revitalize our relationship.

It was really still and there was fog over the lake. It’s a Great Lake, so it’s massive and it was unusual for there not to be at least some waves. We were sitting on the beach under the cliffs. She seemed happy and asked why I had wanted to come here. I explained my reasoning to her. I looked over to her and her face was in her hands. She said she wanted to break up.

So yeah, that was rough. But it’s been a few years, so now I can look back at it and laugh.

FrenchSnail

34. Diamonds Are a Man’s Worst Enemy

I wanted to do something romantic and exciting for my wife, so I surprised her one evening by bringing home a pair of diamond earrings that I had secretly bought for her. She opened the package and immediately said: “But they’re not the same cut as my ring, I can’t possibly wear these!” Not even so much as a thank you.

Suffice it to say she is now my ex-wife…

brockhopper

35. You’ll Find Out Where We’re Going When We Get There

When I first started dating my now-wife, I thought it would be romantic to surprise her with a private fireworks show for her birthday. So, late at night, I drove her out to the spot in the forest of an unfamiliar state where the arrangements had been made. I somehow never anticipated the fact that this situation would make her think I was trying to murder her, but it did!

yelrambob619

36. Having a Ball

My friend once had the bright idea of trying to be romantic by asking a girl to prom with a whole crazy stunt. He held up a sign in the middle of class one day, stating that he “finally got the balls” to ask her out. The rest of the class was then prompted to pelt her with crumpled balls of paper while he waited eagerly for a response. He did not like the response she gave.

Word of advice, try not to be so literal with that kind of stuff, especially if it’s private part-themed!

Scrambled_Toast

37. Crash Landing

Back in college, I once booked a spontaneous romantic trip to Europe for my girlfriend and me during a long weekend. It backfired when we realized that, apparently, we both get grumpy as can be on long flights. We basically just spent the weekend fighting, so it was definitely not worth spending the little money I had on…

georgegsmithjr

38. A Shot in the Dark

My ex-girlfriend collected shot glasses. I came back from a trip across Europe with a bunch of different unique shot glasses from small towns in France, Italy, Spain, and Malta for her. I thought it was a really romantic and thoughtful gesture that she would definitely appreciate. Nope. In her eyes, the gesture meant I was coming on too strong, and the relationship soon ended because of it.

I’ll probably never do something like that again out of fear.

Resteej

39. Not Very Relaxing

I got my very anxious and overly stressed out ex-girlfriend a spa package of three deep tissue massages at a place where I had gotten a couple of massages in the past. It was her first massage ever and she really enjoyed it. Then, a few months later, it was reported on the news that the owner and proprietor of that spa had secretly been abusing and threatening women while giving them massages.

That didn’t exactly help my girlfriend’s stress levels…

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40. A Change of Plans

During my sophomore year of high school, I was pretty involved in my school’s drama department. Yeah, I was a lame kid, I know. There was a girl who I had befriended the year before who was now a senior, and this was all back when I was naïve enough to think that grand and bold romantic gestures were a good idea.

So, I basically got most of my class in on the gig: asking her to be my date to the homecoming dance. I had two main ideas, the first being pulling a Top Gun and getting all the dudes to sing the Righteous Brothers’ classic “You Never Close Your Eyes Anymore” with me. Luckily, one of my friends in her year talked me out of that one.

Instead, I had the bright idea to have my friend hand her a parcel addressed to the “Most Beautiful Girl at (insert high school name here)” as she walked into class. I signed my name on the parcel and stood by waiting with a bouquet of roses for when she showed up. Inside said parcel was a hand-mirror with the word “Prom?” written on it.

Well, uh, that didn’t work out quite as planned. I mean, she was nice about it. She pulled me aside and explained how she appreciated the gesture and how it was the most romantic gesture anyone had ever done for her. She then explained that she had already made plans to go solo with her best friends. And she did, and ended up dancing with me for most of the night anyway.

But, I mean, definitely was not the ideal outcome.

bundybro

41. Tackled

I thought it would be super romantic to ask my crush out while we were watching a high school football game together during our sophomore year. She said no, so I said bye and got up and left the game. I thought that nobody I really knew too well had seen this all go down, so I assumed it wasn’t such a big deal.

Then, later that night, I was hanging out with some friends when her brother showed up and told everybody about it like it was a joke. That was almost worse than her saying no.

Jack_Frost21

42. It’s Just Not His Day

This romantic gesture was not done by me, but by my boyfriend. At first, I hated it, but it eventually really grew on me. It all started when, seven years ago, he promised me a mini-weekend getaway for just the two of us. We were going to have a romantic picnic at a secluded beach and then take in an intimate view of the sunset.

I’d say literally every single aspect of the plan backfired. First, he came to pick me up about two hours late. Later, I found out that he had been really busy preparing everything for the picnic. We drove there but, luckily for us, a fourth grade class field trip arrived at the exact same time. We quickly tried to find a place somewhere else. When we found a spot, my boyfriend told me to go ahead alone.

I then looked back and saw him pulling an enormous cooler, barely budging because of the heavy load. When I hurried over to him to try and help, the cooler tipped over and all the ice and contents fell onto the sand. He quickly started shoving everything back inside, cursing under his breath and saying sorry over and over again. The section of beach we found turned out to be dirty. The water looked like sludge and there was graffiti all over the rocks behind us.

The drinks and fruits were covered in sand and the sandwiches had water in them from the cooler. We later realized there was sewage in the water, which was why there was a horrible smell and a disturbing amount of flies around us. Needless to say, we didn’t stick around till sundown. He didn’t have money to buy anything else because he had spent it all on ice and drinks.

I paid for our Burger King meals. I hated this whole experience and thought it was literally the worst date that I had ever been on. However, later that evening I went home and realized how hard he had tried to make my first “real” summer date special. Despite everything that went wrong, that really meant a lot to me and I decided to give him another chance.

Seven years later, we’re still going strong!

ketzzy

43. Hiding in Plain Sight

In what I thought at the time was a pretty romantic gesture, I gave my long-time high school crush a walkie-talkie on Valentine’s Day because she had to babysit that evening at a house near mine. This was before the days of cellular phones. I hid in the bushes and talked to her on the walkie-talkie almost all night.

Towards the end of the night, some neighbors didn’t take kindly to seeing some sketchy teenager skulking around the neighborhood with a walkie-talkie. It wasn’t long before someone called the cops on me. I lived in a small but affluent town; so whenever the cops were involved in something, more than enough units showed up to respond.

So I’m sitting in a bush talking to my crush about Pearl Jam or something really stupid, when all of a sudden five cop cars come speeding down the block, slam on their brakes in front of my hedge, and light me up with the spotlight. They order me over their loudspeaker to come out with my hands up right away.

Note that this was a quiet suburban neighborhood at the crack of 11:30 in the evening, so everyone in the area quickly realized that something was up and started turning their collective attention towards me. I ditched the walkie-talkie into the bush because I didn’t want to take my crush down with me and shimmied out of the hedge.

I’m now standing with a bunch of cops at the front of one of the cars. The police lights are still on. More and more neighbors are coming out to watch, as well as peeking through their blinds, but somehow I remain calm, cool, and collected. After all, this was all in the name of love, right? It couldn’t possibly turn out badly for me!

I explained to the officers that this was merely a romantic gesture for my “girlfriend” gone totally wrong. For some reason, I thought that if I told the cops she was my girlfriend, they’d go easier on me. So, they have me fetch the walkie-talkie from the bushes and I give it to the main cop. He was such a jerk!

He immediately picks up the walkie-talkie and says into it, “Hey there, is (insert my name here) your boyfriend?” to which she responds, “Ummmm, definitely not…” That was when I realized that the gesture had backfired. Honestly, there was a lot more to my exchange with the police after that. But to make a long story short, they just let me go in the end so that I could lick my pitiful teenage rejection wounds.

The girl and I continued to stay friends after that. I still retained my crush on her, but I knew where we stood and didn’t try any further stunts of this nature. From that night on, the neighbors probably all thought I was some kind of a weirdo and never looked at me the same again. I would imagine that they all cheered on the day I left for college.

millenialskilledme

Romantic Backfired FactsPublic Domain Pictures

44. This One Kills

I worked with this girl at a Ruby Tuesday restaurant. For her birthday, we all went out for drinks. We were all friends and I think she knew that I liked her at the time, though I hadn’t made a move yet. She gave off this rocker vibe. She had tattoos and dyed hair. She loved 80s hair, metal, and rock music in general. So, for her birthday, I decided to burn her a CD of all of my favorite songs from the band “The Kills.”

I chose that band because its lead singer, Alison Mosshart, kind of reminded me of her; and I thought that their music would be right up her alley. So, I burned the CD on my computer, decorated the CD cover with a sharpie, and 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. A close buddy of mine from high school also happened to be working that day. I came in the following day for work and he immediately pulled me aside. He said, “Dude, you should just forget about her.” He went on to tell me that she had basically just trash-talked and made fun of my gift behind my back.

Apparently, she had said to my friend, “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. He proceeded to defend me, saying: “Are you kidding me? You should be so freaking lucky and thankful that anyone gives a darn about your birthday at all!”

As soon as I heard about that incident, it immediately killed any and all interest that I’d ever had in her. How can I possibly be attracted to someone who cares that little about other people’s feelings? She never even bothered to thank me for the CD at all. She just never mentioned it, so I decided to move on with my life and forget about her.

The_Iron_Zeppelin

45. A Slight Change of Plans

I had been dating this girl for several years. Let’s call her “Ann.” We met while working at the same company and things were going really well between us. So well, in fact, that I thought that it was time to pop the question. So, after asking her dad for permission, I planned a whole romantic evening for her, which was going to culminate in me pulling out a beautiful ring after dinner at a very nice restaurant and surprising her with my proposal.

Now, I’m going to take a short pause to talk about another man. Let’s call him “Joe.” Joe was transferred to our branch probably about six months before I decided to propose. He was one of those guys who was being groomed for upper management, and he was transferred to our branch, I’m assuming because my manager was getting pretty up there in years and Joe was a prime candidate to take his place.

Fun fact about Joe: His left eye was all foggy and glazed-over looking. It looked like it had a white film over it, but apparently he could see fine out of it. Another fun fact: Joe was a terrible person. He was one of those guys who sucked up to people he wanted to impress and was a complete jerk to everyone else.

Anyway, back to my original story. I had done all of the preparations I was supposed to do. The big day finally came. Ann looked crazy nervous throughout the whole dinner, but I assumed she just knew what was coming and was feeling anxious in anticipation. As I said, things had been going really well between us.

After the main course and before dessert, I got down on one knee in the middle of the restaurant and proposed to her. She said no. Apparently, she had been secretly dating Joe for several months and was planning on breaking up with me, which she proceeded to do right then and there. In front of the whole restaurant. And then she left. The waiter gave me a free dessert.

It was still pretty brutal. Not long after, Joe actually got his promotion elsewhere and was transferred. Ann followed him. So now, I am still not married. In other words, as a wise old song once said, “If it hadn’t been for Cotton-Eye Joe, I’d have been married a long time ago. Where did you come from? Where did you go? Where did you come from, Cotton-Eye Joe?”

NotEvenJohn

46. An Idea That Folded

I spent a month and a half teaching myself how to make origami roses because my girlfriend at the time liked origami and was not too big on regular flowers. She had said numerous times that she thought origami roses were really charming, so I thought she would definitely appreciate this kind of gesture. What could go wrong, right?

I hid my plans from her as best as I could. I spent hours on YouTube trying to figure these skills out. I wanted to burn my own house down on numerous occasions because of the amount of struggle involved here. Nevertheless, I saw it through and thought that the final product was going to be extremely romantic, awesome, and worth it.

I made 12 flowers, each with stems and leaves, and each one a different color. When I was finally done, I put them all into a vase and presented them to her. Her reaction was about the equivalent of a shrug and a “That’s nice.” Pretty much zero appreciation or recognition of how much I had put into this. I would also like to point out how ridiculously difficult origami is, and that I have nothing but the utmost respect for people who do this proficiently.

If you are good at origami, hats off to you and I hope that it came more naturally to you than it did to me. I literally wanted to play in traffic for the duration of trying to learn this. That’s how difficult and frustrating it was for me to learn. It’s amazing how something so seemingly simple can be so impossible to execute. I only wish my girlfriend would have felt that way too…

Rambro663

47. Car Trouble

Well, I once asked a girl out back in high school by writing her initials with flowers on her trampoline. I did it overnight, so I expected a reaction the next morning. Reasonable, right? Wrong! See, I had left a note on her car suggesting that she check her trampoline, but she just so happened to have driven her mom’s car to school that day instead.

She even went out for lunch that afternoon and still said nothing when she returned, so I was in full “what the heck have I done to deserve this silence” mode until I realized that she had taken the wrong car. Thankfully, her mom called her in the middle of the day and told her that she needed to come home early for some reason or another.

Before she left, I spoke to her for a couple of minutes and she said we could talk more later that night. I thought this would be my chance for sure. Fast forwards to that night. No response from her to any of my calls or texts. After a while, I finally gave up and went to my buddy’s house to hang out. That was when I realized why she hadn’t been responding to me.

She was over at my buddy’s house, clearly together with some other guy. Since I had never told anyone about my feelings towards her, I then had to spend the rest of the evening pretending it was nothing while silently feeling crushed inside. I played my worst game of pool ever before breaking my friend’s phone after he questioned whether I would seriously do it. I wanted to prove to her that I was serious about whatever I say.

I ended up driving home with sadness level ten.

Kilomyles

48. Recycled Love

When I was in the first grade, I wrote “I LOVE YOU” on a paper airplane and threw it to my crush from across the classroom. Without knowing where it had come from, she caught it, read it, and started to smile. Then, she gave it to the boy she liked. Spoiler alert: that boy was not me. I think it’s safe to say that this little gesture of mine backfired…

lanni957

Airport Goodbyes FactsMax Pixel

49. Too Much to Bear

I was seeing this girl for a while and decided to ask her to be my girlfriend. To be romantic, I went to Build-a-Bear and had a teddy bear made with a voice recording of me saying “Sara, will you be my girlfriend?” inside of it. I then went to her house, gave it to her, and asked her to press the bear’s hand so that the message would play.

When she heard the question, she politely declined because she wasn’t ready for a relationship. But the story gets so much worse. Her family happened to have been having a party in the background while all this was going on. And yes, somehow, it gets worse. While I was still standing at the doorway, her eight-year-old sister who loved stuffed animals saw the bear and walked over towards us.

The kid grabbed the bear out of Sara’s hands and began running around the house pressing its button repeatedly. As a result, her whole family and all their friends then heard my desperate and rejected request getting replayed over and over again. After a couple of minutes, I couldn’t bear to hear my voice asking her out anymore, so I quickly left.

staypearly

50. Business Affairs

I once surprised my fiancée at her work with a bouquet of flowers. She thought it was creepy and told people I had snuck into her office. Security had to change all the codes as a result of this. In reality, I had simply walked up to the receptionist and said I had a delivery for my fiancée, at which point I was politely escorted inside.

At first, I couldn’t figure out why she had reacted like that to my gesture. Then, I found out the disturbing truth. It turned out that she had been having an affair with her boss and was gaslighting me to make me look like the bad guy. At that moment, it all clicked for me because I’d always thought “the only difference between a creepy gesture and a romantic one is how you feel about the person doing it.”

Now I understand that I did nothing wrong.

Benadryll

Sources: 1, 2


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