On behalf of significant others, let me be the first to admit that we don't always think all the way through our romantic gestures. Sometimes this can result in minor inconveniences for your significant other and other times it can ruin anywhere from their day to their next month.
Let's take a look at some other significant others that had great intentions but poor execution.
All posts have been edited for clarity.
Reorganizing The Kitchen
“I have a huge collection of cookie cutters because I love to bake. I kept them immaculately organized in small boxes and bags in the drawers of my kitchen island. Some had small pieces because they were things like snowflakes you cut multiple ways, some had tiny individual letters for stamping messages. I also really have a lot of other kitchen things because I love to cook.
He texted me at the start of an eight-hour barista shift that he was reorganizing our kitchen as a surprise for me and getting everything consolidated. I remember freaking out and begging him to not do it and he was like ‘No, it’s good I promise! It’s too late! Don’t worry!’
And then I got home, and he had dumped all of my cookie cutters into two huge reusable grocery bags, threw out any boxes or bags that were keeping sets and pieces together, so everything was loose and now impossible to find small bits, it was a huge disaster. I still think he threw out some actual cutters because almost two years later I still can’t find some pieces. I cried for hours because I had been so careful over the years with my collection and in one afternoon it all went out the window. Some of them got bent because they needed to be handled with care.
He also emptied out some teas that were ‘old’ which had actually been favorites I ration for bad days. Most of which weren’t made anymore.
I feel bad that I went a little crazy and cried, but he just didn’t get how much he had messed up my collection that I spent years building and keeping neat.”
Lost In Translation
“My now ex-boyfriend and I met while studying in Germany. I left to go back to the United Kingdom and he still had a few more months there until Christmas.
I went back to Germany with a friend from home to visit my boyfriend and other friends a week or so before Christmas. We flew to Hamburg, which was around three hours by train to Hannover where we studied. There were no direct flights to Hannover from the United Kingdom. My boyfriend at the time told my friend and me we should pack one dressy outfit for a surprise.
When we landed in Hamburg, my boyfriend told us not to get on the train to Hannover. Instead, we should go to Hamburg City Centre, get changed in the bathrooms of the train station, and they would meet us there. My boyfriend and other friends showed up so there were six of us total.
The surprise was they booked tickets to see Phantom of the Opera for us! Wow, that was great. I had never seen it before and neither had my friend from home. However, we went to the theater and realized it was in German. Only one other person in the group and I could speak German. Two other members of our group had seen the show before so they could at least follow what was going on. The other two had absolutely no idea what was happening.
On top of that, my boyfriend didn’t realize just how long the Phantom of the Opera show was. If we stayed for the whole show, we would have missed the last train back to Hannover and the next one wouldn’t leave until four o’clock in the morning. It was December, freezing outside, and we had our suitcases so staying in a bar until then wasn’t really an option. We decided to leave the show at the intermission and take the last train back. It was a sweet gesture ,but I felt so bad because he spent good money on the tickets and train fares only for nobody to enjoy the show.
Also, the next day he had booked a brewery tour for four of us. It was also in German, so I had to translate for the other three the whole time.”
“Valentine’s Day. I was a painting instructor at one of those paint and sip places. I just worked three classes back to back, which is around a fourteen-hour day. I was exhausted. My boyfriend at the time picked me up around ten o’clock at night and took me to a mysterious location.
It ended up being a picnic in a field. It was also February in Texas but still icy and frigid by Texan standards. I was absolutely starving after a long day, but he only brought some fruit and Lunchables. I was freezing because I wasn’t dressed to be sitting on the ground in the cold and completely exhausted from work. It was also extremely dark and he was only using his cellphone flashlight. The stars weren’t visible as we were in the city.
I tried so hard to smile and act like I was enjoying it, but I eventually asked him if we could wrap it up and go. That seemed to upset him. I ended up breaking down in tears, saying I just really wanted to go home because I was tired, hungry, and cold.
The thought was very sweet, but the execution was awful.”
“Christmas Shopping For A Female Friend”
“One of my exes, early in the relationship, asked me to help him go Christmas shopping for a female friend. His reasoning was because he didn’t know what women like. He didn’t share any other information other than she was a special friend and he really wanted to make her happy. He thought my input would be best.
We spent all afternoon going from store to store, accumulating a number of expensive trinkets. We picked out a necklace, perfume, expensive candle holder amongst other things. I’d ask about her personality and interests, but he would just awkwardly ask if I liked the item. I’m not into most typical ‘girly’ things though so it all felt like a guessing game to me.
At the end of the day, he revealed all the gifts were actually for me but none of them were things I wanted or could use! I had selected things based on little things he said here and there about this fictional friend.
It was very sweet and I could tell he had put a fair bit of thought into figuring out a way for me to choose my own gifts without knowing it. But the reality was I just spent hours confused thinking my boyfriend was clumsily trying to get help from me to shop for his mistress or something.
He could have just said something like, ‘She’s a lot like you and into the same hobbies, so anything you’d like she’d probably like too,’ It wouldn’t have been nearly as weird as it was. I didn’t have the heart to look into his hopeful, earnest eyes at the end of the evening and tell him he’d spent a bunch of money on stuff I would never ask for and didn’t want.
I’ve never had a partner who put so much effort into surprising me with gifts or romantic gestures so I don’t hold it against him. There were other incidents The fact that he tried so hard to create fairytale or romantic moments, even if they didn’t come out right, made me swoon even if a big part of me was cringing deep down.”
Grand Gesture Loving Boyfriend
“Back in college, I was dating a guy from my home town which was about four hours away from my school, so he would come to visit on weekends when he could. He was supposed to arrive the Friday night before Valentine’s Day and we were going to have a fun weekend together.
Well, he decided to come earlier in the day than he said he would to surprise me, around noon rather than six o’clock. I had a class at that time. I still don’t know what his actual game plan was, but the dude showed up to my two hundred-person lecture with flowers. Most people would have opened the door, realized their plan was flawed because the class was gigantic, and left immediately but no. He decided to stand in the back of the lecture hall in the middle of class and say my name loudly which prompted everyone in the hall to turn around and stare at him.
After a long tense silence, someone in the class said, ‘Uhhh man, I think maybe she skipped class today.’
I had indeed skipped class and was happily eating Chick-Fil-A and watching Netflix in my dorm while this humiliation was unfolding. I had never been so grateful to be a slacker because I can’t imagine what I would have felt if I had actually been in class that day, and had to get up in front of two hundred people and weirdly take flowers from my grand-gesture loving boyfriend. Just thinking of it now makes me cringe.”
Squadron Christmas Party
“I’m in the military, and at the time I had a pregnant military wife who owned a car in poor condition. It was not fit to travel to her family that lived states away.
I worked on my credit score for two years prior and was finally capable of getting a vehicle reliable and big enough to support us and our incoming fetus. This was around Christmas at our squadron holiday party with the newborn.
I decided this was going to be my gift to her that year because I loved being a little extra on events like birthdays and holidays.
I had found the perfect vehicle that was affordable and I could get approved for. It was even exactly the one that she said she wanted. I even bought a giant bow to put on the hood. I got the vehicle a week before the squadron party, and had a friend drive it to test it out and hide it from my wife. It ran perfectly with no problems. I asked my friend to bring it to the party and promised I would give him a ride home. I put the bow on the hood while my wife thought I was using the bathroom.
On the night of the squadron party, I didn’t ask anyone to come and make a spectacle of the situation, they were all focused on the party. I just asked my friend to drive up while I covered my wife’s eyes. He drove up with the vehicle with the bow on the hood and I make the big reveal, ‘Merry Christmas babe, I’m so happy we’re starting a family together and I think this is the perfect investment into our future.’
She looked at me with disgust and said, ‘Really? You had to give me this at your Christmas party? How selfish can you be to make this about you?’
At that point, I felt smaller than a mustard seed.
She didn’t speak to me the rest of the night and drove home in the new car. I took my friend home in our old car and he kept apologizing like it was his fault. I felt terrible all around.
Unfortunately, we didn’t make the marriage work and there were a slew of other things that were red flags to her personality that unfortunately, I didn’t know until too late.”
“My ex-boyfriend planned a double date for my best friend and me. We were so excited because our respective exes talked it up and told us to dress up.
Upon arriving at the restaurant, we realized we were way overdressed. Both of our exes were also plastered. In an attempt to save face and make it romantic, they stole all the candles off the other tables so we had a table full of tea lights.
They had already ordered food and drinks for us when we arrived; however, they had forgotten we were both vegans in their plastered state of mind. On top of that, there were no vegan options other than salad and sober drinks. My friend and I couldn’t eat a single thing that they ordered for us.
Our relationships lasted a few months after that date.”
“I meal prep and track my calories and macronutrients. I eat a decent amount of vegetables and lots of protein. My significant other and I were long-distance and sometimes he would get a food delivery service to deliver a ‘healthy’ lunch to my workplace whenever I was upset at something or just extremely exhausted. He would tell me the night before so I wouldn’t need to bring my prepped lunch the next day. I initially thought it was really sweet.
The way I prepped is that I cooked the veggies over the weekend and cooked some meat every morning that I had marinated the night before. He thought all that was tiring to me, hence food delivery service so I would have more relaxed mornings.
But he didn’t realize that I had already planned out my meals for the week and those mystery meals he kept getting delivered to my workplace aren’t as ‘healthy,’ according to my standards, as he thought. For example, chicken with brown rice that was obviously fried in butter or a salad with hardly any protein and lots of dried fruit. I ate them anyway.
I told him I really appreciated the gesture, but to tell me ahead so I can pick out the food whenever he wanted to treat me for lunch.”
“I flew halfway across the world to Vietnam for a twenty-day vacation after going on three dates with this guy.
One evening, I was sitting with my friends in a dingy but awesome restaurant in Hanoi. The house was old and had like five floors and several different dining rooms with long shared tables. Vietnamese and tourists alike ate elbow to elbow. We were having a lot of fun.
Suddenly, there was some kind of commotion. I saw waiters and runners talking rapidly to each other, and going back and forth and it looked like they were looking for someone. It disturbed everyone’s dinner and it took them like half an hour to give up, and the place calmed down again.
When I got back to my hotel and connected to better WiFi, I got a dozen messages from the guy saying he had called the restaurant I was at to ask them to send me a drink and charge it to his credit card. He had seen where I was because I checked-in at the restaurant on Facebook. He said he had spent half an hour on the phone with several members of the staff who barely spoke English, and none of them could understand what he wanted except that he wanted them to look for a girl with short red hair.
I got really mad. I was on the other side of the world having a good time and this guy I barely knew was trying to woo me by buying me a long-distance drink, disturbing the restaurant staff and diners. I’m very reserved and introverted, and I think that if it had worked out it would’ve mortified me.
To this day I cringe when I think about it. He spent a lot of money on that phone call, too.
Oh, maybe I should mention we’re married now.”
“I met a guy, we probably hung out like three or four times for brief, casual dates before he suggested a single night trip away in a city a few hours away from where we lived. I wasn’t sure how I felt about him; I wasn’t physically attracted to him, but he seemed so nice I figured one night away wouldn’t be so bad and maybe things might even go well.
English was his second language, and it was cute until I actually had to speak to him for a few consecutive hours. I realized that a lot of humor went over his head because he didn’t quite understand what I meant, and a lot of what he was saying didn’t make sense and he would get flat out frustrated that I couldn’t understand him.
When we finally got to our hotel, we went up to the desk. He told the receptionist his name and she said, ‘Right, so, we’ve got you booked in room 574 for three nights, enjoy your stay!’
He had decided on a whim when he made the reservation to make it three nights instead of one, without mentioning this to me. He knew I had cats at home and had only made arrangements for one night. I was horrified. I ended up having to suffer through the trip, I was miserable the entire time despite him trying his best to make it fun.
We went to the zoo, and there was a panda exhibit that was just utterly depressing. There was a new baby panda I was excited to see but when I saw how unhappy they seemed, it was enough to break my heart and I just felt guilty being there and seeing all the animals. We rushed through that. Then we went out for a fancy dinner. He told me to dress up and that we had reservations at a restaurant close to our hotel. We walked the streets of this huge city for like forty minutes. He had put in a different restaurant location on his phone’s GPS or something along those lines that basically meant we were lost. I was starving and cranky, and we gave up trying to find the place and ended up in a poutine shop and eating greasy soggy poutine while wearing a slinky dress and four-inch heels.
There was so much more that went wrong on the trip and it was the longest four days of my life. I still physically cringe when I think back on the whole thing.”
Backpacking Around The World
“We were backpacking around the world and landed in New Zealand for a year. We were finally getting our lives sorted, and had moved into a small studio apartment.
I had recently purchased leather shoes which were my first new shoes in three years! I’m an avid shoe collector and I keep all my shoes in their boxes.
Anyway, I came home from work on Valentine’s Day to find my shoebox cut up and turned into a waterproof shower shelf as I had complained that we didn’t have one. My Ruby-Woo MAC lipstick was also used to write how much he loved me on the shower wall. That was the only makeup I had bothered to take overseas with me.
It was super kind but also very devastating at the same time. I laughed, took photos, and ended up being very thankful for that shower shelf.”
“My boyfriend was a wonderful guy, but he had heart problems and was told by doctors he wouldn’t see thirty-years-old if he didn’t quit caffeine.
Well, he told me this early on in our relationship and being dumb and nineteen-years-old, I kinda forgot about it after a few months beyond, ‘He can’t drink coffee and caffeinated sodas.’
For our first Christmas, I wanted to be sweet and dorky and got him a giant tin full of Hershey’s Hugs and Kisses. As you might know, even though I didn’t consider it, chocolate does have caffeine.
My boyfriend realized it, but since he was also dumb and young, he still ate them because he liked me and the chocolate was right there.
Which is how we spent an evening near Christmas with me panicking and sobbing my apologies as he struggled to breathe while his heart did a creative drum solo.
The story has a happy ending though. He survived the night, I partnered with him in quitting all sources of caffeine to keep his heart healthy until he felt comfortable abstaining on his own. A decade later, his heart showed no sign of the previous trouble and he was cleared to have caffeine again. At thirty-four-years-old, we’re still happily together and he can enjoy coffee and chocolate like normal people without fear.”
“It was recently my birthday, so my significant other ordered flowers and bought my favorite perfume. Unfortunately, the flowers were delayed and didn’t arrive on my birthday. So instead of just giving me the perfume and telling me flowers were coming, my significant other decided the best course of action would be to pretty much ignore my birthday completely other than saying happy birthday. I spent the day crying and mostly alone.
The flowers arrived the next day. My significant other and I got into a fight because he couldn’t understand why I was mad that he let me spend my birthday upset when I didn’t have to. Also, I’m not really into flowers, so the money spent could have been spent on something else.
Yes, he meant well but he just handled it so badly. I hate my birthdays because they always suck.”
“Stole Her Brother’s Car And Drove To Maine”
“My ex-girlfriend stole her brother’s car and drove to Maine. She moved into my family’s cabin and decided she was going to fix it up for the two of us to live in.
Unfortunately, I was dating my now wife at the time and we went up for a weekend only to find a cabin filled with all of my ex-girlfriend’s clothes and personal belongings. It was quite a shock to me!
My ex-girlfriend had found a job at a local FM radio station as a disc jockey. I eventually contacted her there and told her to get all of her stuff out of the cabin. She did.
I’ve been married to my now wife for thirty years now.”
Folded Up Pink Paper
“When I was fourteen or fifteen, my first boyfriend gave me a small square of folded up pink paper just as he was leaving the house. He told me to open it very slowly and carefully and then he left. I was so excited about this bit of paper I could barely contain it, but I still forced myself to stand on the doorstep and watch him walk away until he was out of sight like I always did.
Then I rushed inside and unfolded the paper, hands shaking, thinking maybe there was glitter in there. Why else would he have told me to unfold it slowly? It had been folded so many times and the whole process felt like it went on forever. Finally, I reached the end of it and there was absolutely nothing. Just a blank piece of paper with crease marks all over it. I turned it over in my hands looking for some small clue. Nothing.
I was so disappointed that I rang him crying. He confessed he made it up because he did not like how I stand on the doorstep and watch him until he’s out of sight and was hoping that unfolding that piece of paper would distract me from doing it. I felt embarrassed, of course, because I thought it was our romantic thing. However, I did remember how he had hesitated before he left. He had probably already realized how his plan would backfire. Anyway looking back after all these years, what on Earth was I doing standing there waving and blowing kisses as if he was going off to war each time? The poor guy was probably sick of it.”