Ah, the joy of watching someone's well-intended plan go up in flames. Whether it's a date idea gone nightmare-wrong or a first impression that got completely boofed, these stories aren't about people with foot-in-mouth syndrome. It's more like the whole dang leg. Strap in and get ready to cringe, laugh, and cry at these epic backfires.
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…
2. The Great Exploding Toilet
I decided to burn some newspaper outside in a toilet I had just replaced because I didn't want to risk the grass catching on fire. Well, heat caused the toilet to explode, sending burning newspaper everywhere. Then the grass caught on fire. Nailed it.
3. 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.
4. It’s the Thought That Counts
I offered my seat to an elderly lady on the bus. Turned out she wasn't that old and felt offended, so she screamed at me for the entire ride home.
5. 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.
6. 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…
7. Bullies Never Learn
When I was a kid, I tried to shake hands with my bully, thinking this mature act would diffuse the situation. Nope. As I went in for a handshake, the bully took his shot and punched me in the throat.
8. 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.
9. Kickfall
This one time in sixth grade we were playing kickball in gym class. I went to a private school, so I was wearing a white polo and grey slacks. Well, I had just started playing football so I was bragging that I could kick the ball really far. Mind you I was the short little pudgy kid everyone picked on. Well, I was up to kick, I pointed way into the outfield, ran at the ball and tried to kick it realllllly hard.
Well, not only did I completely miss the ball, I farted really loud as my leg fully extended and ripped my pants and underwear down my butt, then I fell right back into a puddle of mud. Everyone started falling over laughing, even the gym teacher who pitched the ball to me.
10. 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. Years later, that one still hurts.
11. DOES NOT COMPUTE
I personally don’t speak Chinese, but I dated someone who did. I worked with a dude who had a BIG tattoo all down his back in Chinese lettering in remembrance for a friend who had passed. He thought that the characters said the friend's name. My date said that the tattoo translated to “does not translate/ untranslatable.” This poor dude had plugged his friends name into google translate or something and it came back unable to translate and since he couldn’t read the characters that’s what he printed out and took to the tattoo shop.
12. 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…
13. 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.
14. Kidney Failure
A lady in my office donated her kidney to her boss to save his life, only to be fired shortly afterwards. Good luck beating that backfire, folks!
15. 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.
16. Chubby Chaser
Dude was so proud of his grandson that he wanted a tattoo that said “I love my grandson” in Chinese characters. Except I’m guessing everyone just googled “I love my grand son” because it came out reading “I love fat boys.” Whoops.
17. 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.
18. 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.
19. Taken for a Ride
I flagged someone down on the highway who was driving with a flat tire. We both pulled over, and they explained that they didn't have a spare. I offered to drive them to the closest convenience store and back for a can of fix-a-flat. Not only did they ride in my car silently, offering no thanks at any point, but they also stole my wallet out of my console when I wasn't looking.
20. 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.
21. It’s Just a Prank, Sir!
For April Fools, I was planning to do an innocent prank by putting an air horn under my teacher’s chair so when he sat down it would trigger it and startle him. Nope. My idea could not have gone worse. The bus driver sat down on the air horn, it went off, he got so startled that he jumped out of his seat, landed on his back, and got knocked unconscious. The school told my mom what happened and I got grounded for a week.
22. 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!
23. 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.
24. A Warm, Wet Lesson
When I was a kid I took swimming lessons. One day after lessons were done and we went to the locker rooms to change there were some clothes sitting on top of one of the sinks. Me, wanting to show off, decided to push the clothes into the sink and turned on the faucet and soaked the clothes completely. We all had a great laugh.
So I got to my locker to get my clothes and made a horrifying realization. My clothes weren’t in my locker. That's when I realized that the balled-up pile of clothes that were now soaking in the sink were actually my clothes. I sat in my wet swimsuit until the locker room was empty. When my dad finally came in, I lied and said someone soaked my clothes.
He went up to the counter and grumped at the workers until they gave him some clothing from the lost and found bin. They included ugly sweats that were so big they went above my head, and I embarrassingly walked through the center and parking lot humiliated by my own actions. I’ve never told my parents who really soaked the clothes.
25. 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…
26. The Cool Guy Squint
My physics teacher told the guys of the class that one of the best ways to look cool in front of a girl is to do the thousand-yard gaze or looking into the distance. He continued to tell us that girls would think "that guy is so deep, so cool, what is he thinking?" Well, I tried that in front of a girl I had a crush on. Her reply shattered my confidence in pieces. All she said was, "Why are you squinting so hard?"
27. Feeling Good, Looking Better
After losing some weight and getting over some shyness I decided it was time to put on a black dress, heels and head out. As I walked to my car, a group of guys driving by honked their horns. They all waved and whistled and I thought...wow maybe I am looking great. So naturally, the next thing that happened included me tripping in my new heels and face-planting in front of them.
28. Hitting a Wall-et
A woman dropped her wallet in front of me while walking down Broad Street in Philly. I ran fast and caught up with her just in time to return it before she got away. She then accused me of not only taking her wallet, but taking the money that was supposedly in it. It was a good day.
29. 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.
30. 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...
31. Too Close for Comfort
My wife had a coworker who was young and had many addiction issues. I forked over a few grand to help him get into an excellent rehab program instead of paying off the debt on my wedding, putting a lot of financial stress on my own family. Before the rehab place had an opening for him, I walked in on him in bed with my wife.
They moved in together shortly after, and have two kids together now.
32. Dirt Bag Disaster
In my first apartment, I had a bag vacuum (as opposed to a canister vacuum), and the bag was full. I had no replacement bags, so I used painter's tape to attach a Walmart bag. I thought I was a frugal genius and patted myself on the back as I switched it on. It didn't work at all. Almost immediately the bag blew right off, and a bunch of dirt blew all over the place, including all the dirt that was stuck in the vacuum, since the previous bag had been so full.
33. 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.
34. Getting Hitched
On a rainy day, I once gave a ride to a hitchhiker near campus who looked like a typical university student. I normally don't pick up hitchhikers, but it was hard to ignore him standing there in the pouring rain. I drove beyond where I was headed to get him to his stated destination—a place that was pretty darn far off the beaten path. But then he would not get out of the car. He just kept staring at me and telling me that he was "lonely and needed someone to be with." Tried to be nice, got a creepy dude in my car in return. He only left when I threatened to drive him straight to the authorities. Ugh.
35. This Way Out
I tried to dramatically leave and slam the door after an argument in a new apartment. I walked into a bedroom...
36. Thank You, But…
I decided to give myself a mini makeover before I went back on the dating scene. I bought some new clothes, like button-up shirts and nice khakis and was feeling pretty good about myself. Until I went out to show off my new look. Post-“makeover,” I had a lot of people hitting on me. There was just one problem: They were all men. Since I’m a straight man, that wasn't really the result I was hoping for.
37. 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.
38. 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!
39. Brit in Disguise
I am a pizza delivery driver and I get bored a lot. Sometimes when I'm doing deliveries I like to play this game with myself where I talk in a British accent. So I go up to this house and this super hot girl answers the door. I start talking in my best British accent and she freaks out and talks. Turns out she's British, too, and she asks me where in England I’m from.
The only place I knew in England was London, but I got caught off guard by her question and panicked, so I said Camelot. She looked at me very weird and told me I wasn't British. When I told her about my "game" she looked at me like I was somewhere between a loser and a freak. I did not receive a good tip that night.
40. 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!
41. A One-Man Open Sleigh
In college during the winter, we had a heavy snowstorm one year. Everyone was walking to class, and I was heading down the outdoor steps to the basement where my class was. A girl was walking in front of me. She slipped and began to fall. Without thinking, I reached my arms under hers to try and prevent her from falling.
In doing so, I slipped and my legs went forward under hers. She landed on top of me and literally rode me like a sled down the stairs. She then stood up and just walked away. Never helped me up, never said "thank you," never even asked if I was okay. That hurt. Badly.
42. 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.
43. Fleeing to Taipei
My stepson bought an entry level tattooing kit, spent a while practicing on pig skin, and then proceeded to spend much of the winter tattooing three large Chinese characters vertically on the back of his own thigh. He had made friends with an exchange student from Taipei who nicely translated some stuff for him. I can't remember what the tattoos were supposed to say, some simple motto like "truth, beauty, diligence".
Come spring, when it healed, stepson went to show his new ink off at one of the beaches. We lived in Vancouver at the time, so lots of Chinese people wandering by on a nice, sunny day. But if his tattoo was exposed, they'd look at it, whisper to each other for a few minutes, then walk off snickering. Bad sign. Long story short, he had somehow transposed the characters left to right, so they were actually in mirror image; this explained the confusion and whispered conversations among the passers-by.
But it gets so much worse. The characters he so diligently inscribed onto his own flesh didn't actually say "truth, beauty, diligence", or whatever. His high school friend - now safely back in Taipei - had carefully brushed out for him the characters for "ugly white boy."
44. 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.
45. 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.
46. Ballsy Backfire
I was quite bored one day, so I took a large stick and began acting like it was a lightsaber—this was when I was like 12 years old. Basically, as I was playing around with it, my brother grabbed a stick and joined in. We were fighting with them for a bit when I decided to hit him in the balls because he kicked a ball into my face earlier in the week.
So I thrust the stick at his balls. There was a brick wall directly behind him, and I missed. The stick hit the wall and it jutted back and hit me in the balls.
47. Ladies Man
When I was 13 years old and chubby, I tried to impress my crush with my skiing chops on a church retreat. Things...did not go well. I went straight down a black diamond route instead of winding like you’re supposed to, then ended up in the trees with a broken thumb and some fractured ribs. I had to get taken off the course by an ambulance. My crush was not impressed.
48. 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.
49. Independence
I had just told off my ex-boyfriend, who had been trying to tell me I had become too dependent on him and wouldn't be able to leave. "Screw that," I said, "I am independent. And I don't need you for anything!" Then I dramatically turned to get into my car and drive off...but I had locked my keys inside. Oh, but it gets worse.
The car was still running. I felt like a complete idiot. He had to call and pay for a locksmith because I had no cash and the dude didn't take cards. I will never forget that grin on his face. Dumbest moment of my life.
50. The No-Doubter
I hit my first ever home run in high school and I knew when I hit it, it was gone. We always practiced what we'd do if we hit a no-doubter, so in the split second I had to show off, I flip the bat. The bat flips end over end, hits home plate, then straight up in my face. I was unconscious for 15 minutes and since I couldn't run the bases, they called me out.
51. 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.
52. Wardrobe Malfunction
When I was in high school, there was this guy who I thought was ridiculously cool and I, therefore, tried to catch his attention. I am not now nor have I ever been the type of chick to wear a skirt, but I thought I would give it a whirl so this guy could see me a little more of my skin. One morning I set my trap with this totally cool skirt, and I was feeling all awesome and sexy.
When I walked by him, though, I heard him and his friends burst out into hysterical laughter. I kept walking until I rounded the corner, whereupon I discovered the reason for their laughs. Not being a skirt wearer, I did not understand the physics of butt and backpack interactions—so my loose, short skirt shimmied up along my butt with each "heck yeah" bouncy step I took.
My dorky freshman butt and granny panties were hanging out for all to see. Freaking skirts.
53. 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.
54. A Son in Need
I got into a nasty fight with my dad when he was talking down to me and coming across like I couldn't make my own life decisions as an adult. So, I managed some comeback and left the house. I go to get in my car and drive away, and the darn thing broke down a quarter mile from our house on a hill. That's when I had to call him to come and help me.
55. 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…
56. Material Girl No-More
I was 18 years old, fresh out of high school, and driving my brand-new graduation gift Mustang around town. I was cute and in great shape and perky...and I knew it. Dad sent me to the local hardware store, back when it was an ACE Hardware in a strip center, next to the grocery store, not the Home Depot-style warehouses of today.
I was supposed to get something for him and I was more than happy to oblige. I knew what I was doing. I pulled right up to the front of the store in my shiny red car, got out and could feel all the teenage boys who worked in the store watch me walk in. I sauntered to the counter and said, "I need a such-and-such. Can you help me find it?"
I was helped out by two or three boys who helped me find what I needed. I was followed by them all back to the counter at the front of the store to pay for it, where I smiled sweetly and said to them, "Thanks so much for your help!" I may or may not have batted my eyes a little. Then I turned around to leave the store...and walked smack into a plate-glass window.
Everyone in the store let out an audible, "OOOOOOOH!" and those sweet, helpful boys just laughed and laughed. I knew then and there that I would never be that kind of girl again. God was watching me, all full of myself, and said, "You need a little humility. Here. Let me show you." Lesson learned.
57. 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…
Max Pixel
58. Hi, I’m Stupid
Oof, I knew a guy named Ben who had the worst tattoo backfire of all time. He was obsessed with Asian culture, especially China, and he got a tattoo of his name (as a Chinese symbol) on his bicep. Instead of introducing himself when he was in Chinatown, he'd just point at his tattoo. Here's the problem: Ben in pinyin = “pen” (pronounced pe-hn, which does sound like an Asianfied “Ben”). But “pen” in Mandarin means stupid. Dude introduced himself as stupid for years. As far as I know no one has ever told him.
59. A Little Haircut
One time I curled my eyelashes and sneezed. I learned how to use fake eyelashes that day.
60. 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.
61. V for Victory
I was running my first marathon and it was grueling. I had my name written on my top, so as I was headed toward the last mile, people were chanting my name, strangers cheering me on, my parents were there...it was euphoric. Until the moment it wasn’t. I crossed the line with tears in my eyes and threw my arms up to yell and cheer.
Instead, I promptly vomited all over myself.
62. 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.
63. 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.
Public Domain Pictures
64. Shred the Evidence
I pulled what I thought was my expired credit card out of my pocket, and ran it through the shredder at work. It wasn’t my credit card. It was my government ID card, which I also need to log onto my work computer.
65. 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…
66. It’s the Little Things
I scored an interview for a dream job. I did all of my research about the company, bought a new suit, the whole shebang. I gave the man interviewing me a firm handshake, answered all of his questions easily, and felt pretty confident. After finishing the otherwise flawless interview, we shook hands again, and I said, "Thank you sir." To my horror, she replied: "It’s Ma'am."
67. Nailed It
I still have nightmares about this date. When I was about 20 or so, I got a date with a girl who I really liked, she was exactly my type and I couldn't believe my luck. We met in a local pub for a few drinks and things were great. I was getting all the good signs with lots of hand touching and the like. An hour of pure bliss went by and I needed to pee.
After washing my hands, I went to the hand dryer only to find that it didn't work. I wanted to dry my hands because I wanted more of the hand-holdy stuff. Then I had the single stupidest idea of my life. I thought, "I can fix this!" and put my hand inside the nozzle of the dryer. WHY!? WHY!? Obviously, I got buzzed by the electric heating element, fell back, and cracked my head on the wall.
I didn't get knocked out but I needed a few minutes to sort myself out before going back. I didn't have the guts to tell her what had happened; dumb idea number two. I had a banging headache and I wasn’t quite right. Not much later she made her excuses and left and turned me down when I asked her for a second date. A year or so later I found out she had told her friend that she really liked me, but I went to the toilet and came out acting really weird and she "wasn't up for dating someone on drugs."
68. Good Luck Explaining This One
I was on a road trip with four of my friends and I had been talking up this playlist I'd made for our drive. After reminding my pals that it would blow their mind, I connected the Bluetooth to the car's speakers. For whatever reason, as soon as the Bluetooth connected, it immediately played the last video viewed on my phone. Yup, It was an adult video. Yup, still haven't been allowed to live that one down.
69. 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.
70. 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!
71. Officer Cutlet
Japanese speaker here. I saw a guy who had a tattoo that read "トン勝." Someone told him that トン (Ton) means pig and 勝 (katsu) means to win. He thought that putting them together means to win against pigs (authorities?). He was so wrong. とんかつ Tonkatsu means pork cutlet. I didn't have the heart to tell him.
72. 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!
73. 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.
74. What Goes Up
I was in fifth grade, and the school I went to was across the street from a golf course, so golf balls would end up on the playground. Teachers would try to collect all of them so students wouldn't hurt each other with them. I was standing with friends at the baseball diamond when a couple of bullies walked by and said something smart.
I forget what it was and what I replied with, but I had an amazing comeback and they started to walk away. As a show of victory, I tossed one of the golf balls I had found up in the air and yelled, "See ya!" As they turned around to glare at us, the golf ball came down and hit me in the head.
75. 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…
76. 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.
77. 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.
78. Drive-thru Drive-by
I worked at McDonald's when I was in high school and finally got a better job, with better hours, closer to home after a couple of years there. When I quit, I was annoyed to learn that they wanted my greasy threadbare uniform polo and pants back after I was done. See, I didn't want them, but it seemed cheap and sort of insulting—they were just going to throw them away, same as I would, but they were going to require an extra trip back there for me to do it? No, I don't think so. Screw them.
Keep in mind I was 16 at the time, and apply "I'm such a rebellious free thinker" teenage arrogance to the situation. What happened next makes more sense that way. So, on my last day, I went out to my car, stripped down to my boxers, went through the drive-thru, and threw my wadded-up uniform at the woman working the window.
That's when told her to give them to the owner. The look on her face was priceless. I drove off, music blaring, feeling ridiculously happy and proud of what I had just done, and happened to run into a friend of mine who was also cruising around. I explained why I wasn't wearing a shirt or pants, he laughed and said we should go get something to eat.
Sure, no problem, I'll just change into the clothes I brought, grab my wallet, and...Ah, crud. That’s right. My wallet was still in the pocket of the pants I'd thrown in the drive-thru window. I had to slink back in, sheepishly ask someone to search through the trash for me to find my pants and find my wallet. They did.
I didn't go back to that McDonald's for years.
79. The Deadliest Game
This actually happened to my teacher, she entered an ax-throwing competition and while winding up before throwing, it was behind her head. When she threw it she hit the back of her head with the handle. She knocked herself out and the blade of the ax almost sliced her head.
80. Super Supportive Boyfriend
I was never into makeup growing up and recently decided to take a crack at it. I ended up shoving all of the makeup I got to the back of my bathroom cabinet because oh my god the results were not good. I asked my significant other, "On a scale of 'swamp hag' to 'passable,' how did this go?" He hesitated, and then said, "Recent corpse."
81. 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!
82. Can’t Slither His Way out of This One
I once saw a snake in the grass on my lawn in front of me, so I stopped my lawnmower to try and save its life. I reached down to grab it, and put it in the bush away from my path. In the process, I accidentally snapped its neck.
83. 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.
84. Home, Not So Sweet Home
When my mom got older, she started needing help with basic things, so I tried to be a good son and invited her to come live with me and my wife. Well, that plan backfired big time. It turns out that after my dad passed, my mom developed some intense emotional health problems. To make a very long story very short, she began to get paranoid living in our house, and started hating us for “trying to control her.” She moved out, wrote me out of her will, and died a year later.
85. 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.
Public Domain Pictures
86. Bad Math
I offered to pay for the bill on a first date with a gorgeous girl. She insisted to pay half. I didn’t fight it, but I only had a large bill so I did some mental math, pocketed her money and put my bill in. Anyway, long story short, I did the math wrong and ended up fleecing 20 bucks from her. She sarcastically said, "thank you," and I thought she was being sincere. I'm an idiot.
87. It Runs in the Family
Was at a friend's brother's 21st birthday party and was standing around talking with some other guys. On the driveway, a bunch of girls were dancing to the music. It was a really chill night. But it was about to get a lot chillier. The guy next to me said to the guy on his other side "How about the rack on that blonde chick?" The other guy replied, "That's my daughter.” The first guy mumbled something and left at a brisk walk.
88. 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.
89. The Truffle Shuffle of Shame
In seventh grade, some girl was wearing a Goonies shirt. I had no idea what it was, but it looked like a punk band or something and she was preppy, so my emo self tried to act offended and said, "Do you even listen to the Goonies?" Fail. So much fail.
90. Sweet Disaster
I went on a blind date with a sweet guy that my friends all said was perfect for me. We order a small snack for our coffee and as it's arriving at the table and we're chatting, he pulls out his Nokia phone. Trying to make a lighthearted joke, I say, "MAN, that has got to be the oldest phone I've seen in a while." I really dug it in, trying to break that awkward first date wall. Well, it turns out that it was not a Nokia, it was something much more embarrassing. It was his insulin pump.
91. 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?”
92. Kind of Had it Coming
I knew a guy who had "変態外人" tattooed on his arm. He said it meant "Lover of Asian Beauty" when in fact it means "Foreign Pervert."
93. An Old One and Not a Good One
This was in high school. She invited me to her house to have dinner with her family and I didn't know them very well yet. The conversation turned to names we thought were old-fashioned and ugly-sounding. We all threw out a few like Gertrude, Bertha, and Eugene, and then I said the one thing that ruined everything.
I said, "At least that one's not as bad as Deborah!" I used my ugly voice and everything. Her mom's name is Deborah. Her grandmother was also at the table with us.
94. 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…
95. 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.
96. 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.
97. Soup Lover
I don’t speak Chinese but back in college I knew a guy who liked to brag about how cultured he was when in reality, he was just an idiot. He came back from China with some characters tattooed on him. My friend next to me burst out laughing. The guy got kinda annoyed and said "It says Strength, Wisdom, Passion."
My friend then reached into his bag, pulled out his phone, opened up one of those AR translators, pointed it at the guy's tattoo, and through the magic of AR, revealed it actually said, "chicken with noodles." My friend then said that one of his mates in China told him that a lot of Asian tattooists will often deliberately mess up tattoos and stuff because they get really annoyed at those people coming over asking for random words to be tattooed onto them.
98. Housing Crisis
I moved a friend of 22 years out of her house with a husband who beat her, placed her in a spare bedroom in my house, bought her clothes, got her a job, and gave her money to buy the things that she needed. I even took her to doctors' appointments or anywhere else that she needed to go. Then, I found out 4 months before my wedding that she had been having an affair with my fiance every day while I was at work.
I lost my house (which was in his name), along with the $10,000 I had put into re-modeling it, my jeep, and all the money that I had already spent on the wedding. They now live there together, and she doesn't even work. It's safe to say that good deed backfired.
99. Good Grief
My mom and I ran into a couple whose eldest son just died—and my mom managed to make the worst comment possible. Starting a “friendly” conversation and trying to be nice, my mom's "be sympathetic" plan backfires immediately when she starts out with “Must be nice to have the house to yourself! More time for Church!” The conversation just devolved from there. She ignored all hints to drop the subject, including the mother stating they hadn't been back to the church since their son died. The couple was obviously horrified. It was so brutal.
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