Embarrassed People Share The Dumbest Thing They’ve Ever Done To Impress A Guy Or Girl

Love is a tricky thing. There isn’t really a definitive guide on how to act properly when you’re faced with it. You could do everything wrong and still be right, while conversely, you could do everything right and still be wrong. It’s hard to predict what will happen because everybody has different experiences.

Everyone’s got their own little secret track record of cringe-inducing moments when it comes to love. They’re the kind that can keep you up at night and make you shiver upon the thought of them. Unfortunately, no matter how hard we try, we’re all bound to face some sort of embarrassing situation at some point or another.

People of all ages and backgrounds were asked to share the most embarrassing things they did in the name of love, and the results were nothing short of glorious. So get ready, because what follows is a massive compilation of hilarious love stories.

Don’t forget to check the comment section below the article for more interesting stories!

#1 She’s Number One 

During my senior year of high school, I told one of my best friends (who was also this very sweet, very beautiful football-playing boy) to throw the football as high as he possibly could and I would catch it. I thought I could impress him and make him realize that I was the girl of his dreams. Long story short, he threw it really high, and I did not catch it.

Instead, I fractured my pointer finger when it bounced off my hands. I had to wear a finger cast to school for a few weeks and go to physical therapy. He felt terrible, and I felt like an idiot. He did buy me ‘I’m sorry’ flowers though, so that was nice. People at school thought my finger brace was hilarious. I was constantly walking around school giving a “Number 1” hand gesture to people, and everyone started gesturing back at me when I walked by them. Good times.



#2 Everyone’s Invited (Especially Him)

This past year, I threw a fairly large college house party just so the guy I liked could attend. I didn’t want to show him too much favoritism, so I tried to run around and talk to everyone like a main host would naturally do. Luckily, my best friend kept him company and acted as my faithful wing woman. The night ended with me and my crush talking outside, getting closer and closer until he asked me if I threw the party for him.

Even being tipsy didn’t soften the blow of straight awkwardness. I tried to laugh it off and deflect, but I’m a terrible actor. Looking back, it was kind of obvious the entire party was an excuse to see him because it was common knowledge that his favorite book was ‘The Great Gatsby’ and my entire party was themed after it.



#3 Went Through Civil Unrest 

I lied and said I had experience in journalism when I’d only taken one class in college. We didn’t really have anything in common, so I had to think of something that could link us together. On our first date, he took me with him to report on a local clash between the police and a couple of rowdy citizens. I got tear gassed and robbed.



#4 I’ll Suffer With You 

A guy in my elementary school liked a girl with glasses, and he didn’t want her to feel like an outcast. So, he would come home from school every day and stare right into a lightbulb to try to damage his eyes. He thought his parents would have no choice but to buy him glasses. Unfortunately, his plan never worked.



#5 I Got This I Swear 

I dated a gymnast in high school. One time, we went to a park, and I was intrigued by a couple of parallel bars that I saw. They were designed for stretching, but I was convinced I could do a handstand on them, even though she kept insisting that they were too far apart. When I attempted the handstand, they were indeed too far apart, and I collapsed downwards, jamming my chest past my hands and tearing all the ligaments holding my muscles to my breastbone.


#6 Should’ve Listened To Those Anti-Smoking Ads 

When I was a teen, I took Tae Kwon Do classes and there were two beautiful girls around my age. They liked to hang out behind the mall before class and I wanted to impress them, so I went out there with them too. The problem was, once I got there, it smelled absolutely horrible because of these two dumpsters that were wide open nearby.

When we went back to the gym, we started doing our warm-up laps and I felt very queasy. I immediately ran outside, right next to the Dairy Queen, and hurled all over the front window. The staff and guests inside the restaurant all looked shocked and disgusted at me. It was one of the most embarrassing moments of my life.


#7 It’s All In The Hips 

I took my friend to the driving range. She asked if her insanely hot friend could come as well, and I said sure. She told me that she had never hit a golf ball before, so I thought this was my chance to impress her. We got to the range and I hit a couple of warmup shots while she got her clubs from the rental stand. She then stood at the spot next to me.

I decided to really crush a ball to impress her. I gave the swing everything I had but ended up missing the ball and clipping the ground. The club broke right off the pole and proceeded to bounce back to smack me in the face, all while she was watching. For the rest of the day, I had this huge shiner on my face, but at least I made her laugh.


#8 If Only He Had E.T. In His Basket 

My first serious girlfriend was home alone and I thought it might be the day. l was 13 years old at the time, hormone-addled, and obviously confident that she was the love of my life. It was mid-summer and I planned to ride my bike to her place, which was only three miles away. I told my parents I was going to see my friend right around the block, but they warned me that a thunderstorm was rolling in. Stupidly, I ignored them.

Ten minutes later, I was only halfway to her house. I was terrified and crying, peddling as hard as I could to go against the wind. My all-metal framed BMX knock-off was a huge target for lightning, so that freaked me out even more. Thirty minutes later, I finally pulled into her garage. Her parents then pulled me in to get me out of the rain.

I told them this was the only house I knew on the street and that it would have been life-threatening to bike the rest of the way home in this storm. They smiled, knowing it was a lie. They treated me to a dinner which was nice but also extremely awkward because they definitely knew of my intentions. Then they drove me home, not saying a word to me the entire way.


#9 Unintentional Stormchasers 

When I was a senior in high school, I was giving this girl a ride home in a bad storm. Just as I assured her that everything was okay, my windshield wipers stopped working. Then, we heard an emergency broadcast on the radio that warned of a tornado which had touched down less than a mile away from us. I stopped under a bridge and let her cry while I put on my brave face.

I was so scared. That was the second time I had gone through a tornado situation. We literally couldn’t see anything at all through my windows because the rain was coming down so hard. My car started moving because the wind was so strong. It was the scariest experience of my life, but luckily we both made it out alive.


#10 Feel The Wind On Your Face 

My sister was driving me back to college after Thanksgiving break and on the same road, there was this cool girl who drove a yellow Jeep Wrangler. At some point, she came up next to us in the left lane. Of course, I thought, it had to be her! I was in the passenger seat and decided it would be a great idea to open the sunroof, stick my head out, and say hello.

Mind you, we were going about 60 mph and I had my glasses on. I opened the sunroof, stuck my head out, turned to face the upcoming car, and my glasses FLEW right off my face. I’m practically blind without them, so I started to panic. I yelled at my sister to pull over, and we spent the next 30 minutes wandering around the side of the highway trying to find my frames.

They got pretty smashed up, but luckily the lenses weren’t too scratched. I was able to get some duct tape and a pair of sunglasses at a gas station and rig up the monstrosities, but I had to wear them for the rest of that semester since I had no money to buy a new pair. To this day, I still don’t know if it was her driving that Jeep.


#11 A Broken Nose Is Sort Of Tough, I Guess 

When I was 15 years old, I dropped a heavy book on my head. It was an old dictionary; a single volume that was easily eight inches thick and probably weighed 15 lbs. I laid down on the floor, held it over my head with my arms fully extended, and dropped it right onto my forehead. I guess I thought it would show my crush how tough I was?


#12 A Legendary Faceplant 

I was alone in a park that was across the street from my house. I was standing by the monkey bars just fooling around when I saw a group of five girls cycling towards me, all about 16 years old. Thinking I could impress them, I jumped on the monkey bars, still making eye contact with them. Suddenly, I completely missed the bars and fell from a six-foot wooden platform, flat on my face. They ran over and asked me where I lived so they could carry me home. They were really sweet about it but it was pretty embarrassing for me.


#13 Yes, That Is The Actual Hedgehog 

I bought a hedgehog from someone to give to her, but her parents said she couldn’t keep it. I was very young at the time and didn’t really think it through. I just thought, “She’s going to definitely like me after this.” At no point in my planning did I take into consideration the parental factor. It all ended up okay though — I kept the hedgehog and he was the sweetest pet ever. He lived for 7 years!


#14 Specialized Pizza Delivery Ends In Disappointment…But It Gets Better 

He mentioned he liked this little independently-owned pizza place across town. We were in college and I didn’t have a car, so I took a bus across town to pick up a pizza and bring it to our informal club meeting. It took like, an hour on the bus and the pizza was definitely cold by the time I got back. When I offered him some, he turned it down.

I later learned that he was a super picky eater and didn’t like any of the toppings I got. Thankfully, one of my friends helped me eat it because it was so big. I must have impressed him some other way, though, since we’ve now been together for almost six years! It’s funny how love works — you just never know what can happen.


#15 “Do You Understand?” 

In my sophomore year of high school, I asked a girl out on Valentine’s Day by having red, pink and white carnations delivered to her homeroom. I walked by her homeroom, and my buddy signaled at me by shaking his head. Already disappointed, she came out and told me she had a boyfriend. She kept on repeating, “Do you understand?”

In retrospect, I probably had the “deer in headlights” look on my face. The worst part was that I was pretty confident about her saying yes and I had told all my friends about it. The train ride home that afternoon was pure torture as my friends made fun of me non-stop for the entire ride. In my defense, she had invited me to her birthday party a few weeks before and her boyfriend wasn’t there. To say I was gun-shy after that would be a major understatement.


#16 Try And Top This, Boyfriends 

On the fourth of July, after going out to dinner, I took her out on the lake in a canoe to watch the fireworks. It was awesome. Young macho me, of course, turned down her offer to help with the large canoe and I manhandled that thing like it was nothing. I put her in it while it was on the grass and continued manhandling it to show off just how strong I was. The next morning I had to call into work sick because my back muscles were so strained I couldn’t get out of bed. My back was sore for over a week!


#17 Going the Extra Mile...Literally 

In high school, a few hours after school was let out, I was talking to this guy I had a crush on. He mentioned that he left his Spanish notebook in his locker and had a test the next day.  Obviously, I offered to help him out. I walked a mile to the school, went to his locker, called him, got his combination, and read 10+ pages from the notebook to him while I sat on the hallway floor.


#18 At Least He Had A Beautiful Voice 

When I was abroad in the Dominican Republic, there was a dance competition on the stage at the resort where I was at. Anyone could enter as a contestant and there were around 200 people in the audience. I was about 10 years old and spotted a cute girl who must’ve been around 15, so obviously, I convinced myself that the best way to get her attention was to get up on stage and dance my heart out.

Queue three minutes of awkward shuffling, while maintaining constant eye contact with the girl, and horrified looks from my parents. The coordinator cut me off early by pretending the speaker stopped working. I got a pity clap. That moment is definitely up there on my list of most embarrassing moments in my life.


#19 Gotta Go Faster 

I tried to razor scooter down the steepest hill in town while a girl was watching. I crashed into the back of a funeral hearse and shattered the back window. There was a body inside and the family had seen it all happen right before their eyes. I got up, covered in blood and glass, grabbed my scooter and hobbled away to the nearest alleyway.


#20 Instant Rejection Is Not A Fun Thing 

I was 14 years old and totally in love with this girl from my class. We kinda flirted for a year but got nowhere. She was the kind of girl who liked the attention, so you can imagine how she kept me hooked onto her knowing I had no chance. Since it was getting close to Valentine’s day, I decided I was going to impress her by learning how to play guitar.

After a whole week of practicing like a madman, I was able to learn two songs that I knew she loved. Convinced I’d hit jackpot, I courageously went to her house, called her out told her that I had a surprise. She popped her head out of the door, saw me and my guitar and went straight back inside, all while telling me to go the heck away.


#21 Night Goes Very Wrong 

My crush and I organized a surprise party for our mutual friend, which was to take place before we all went out for a bar crawl. I had hoped to show her that I could be a pretty cool guy by helping out with the surprise and cooking a pretty good meal. Instead, I ended up getting blackout tipsy at the bar crawl and apparently, I tried to push her into a frozen river. Not such a ‘cool guy’ move.


#22 Everybody, Wish Him Good Luck 

I started getting tattoos to look cool and have an excuse to talk to her. It worked, but we only dated for a couple of months. It’s the biggest mistake of my life.


#23 Future Comedian Ends Up Bloodied And Defeated 

In elementary school, I was somewhat of a ladies man. One time at lunch, I thought, “Maybe if I shove this straw up my nose, all the girls will think it’s funny.” So I did it. Ten seconds later, there was blood all over my food because my nose started to run. I had to be escorted to the nurse, as well as see a specialist for a few months afterward. Lesson learned.


#24 Improvised Hitchhiking Often Leads To Lifelong Memories 

She was one of my roommates and we were moving out of our house. I had my pack all loaded up. She asked me where I was going and I told her I didn’t really have anywhere to go… So, I did the smart thing and suggested we both take a trip to Mexico, just for the heck of it. We were together for about 16 years.


#25 The Gesture Was Nice 

In middle school, I commented on my crush’s photo: “Will you go out with me?” I posted the message one word at a time, each on a different post of hers and in reverse order so that it would read as the full question in her Instagram notifications. She told me it was the most romantic thing anyone had ever done for her. I didn’t really keep up with her after that year so I don’t know where she is now, but I know I set the bar pretty high for her future boyfriends.


#26 Nearly Drowned…Totally Worth It 

I was in New Zealand, going to a beach party with some girls from the hostel I was staying at. To get to the party, you needed to take a $2 ferry across an inlet which was about one kilometer wide. I decided to swim it instead, to impress the ladies. About halfway through, I realized I was slowly being swept out to sea. I’m not sure how, but eventually I made it to the other shore, about 100 meters away from the pier.

The ferry had docked about two to three minutes before me, and I just nonchalantly walked over to meet the girls, as if I hadn’t just swum against a current to near exhaustion. It worked and I ended up hanging out with one of the ladies afterward. The only downside was that I still had to pay $2 to get back once the party was over.


#27 I Mean, It Doesn’t Feel Like It’s Broken 

Three years ago, I went snowboarding with this fine lady. She grew up skiing heavily and basically went every winter, whereas I was only able to go maybe one to three times a year growing up. She clearly had the upper hand on the slopes, yet I still did most of the boasting on our way to the hills. Not a good call on my part.

I decided to hit a jump to show her some of the skills that I had talked about. I got off the snowy jump and I lost my balance, landing on my wrist. It broke upon contact and I literally just sat there, wincing and trying to recollect myself. Despite the pain, I tried to hold back tears because there were people watching, including my crush.

I thought it was just sprained, so we went to get a bite to eat and I took a few shots to numb the pain. We continued hitting the slopes for a few hours but as a broken wrist would have it, the pain was pretty bad. I come to find out later that it was broken so badly that I needed a few screws and a plate in my wrist.


#28 Luckily, Nobody Was Hurt 

I was about 12 years old and riding my bike home from high school when I saw a pack of pretty girls ahead of me, about 5 years older. For some reason, I thought I’d be cool and overtake them by dropping down into the road and then jumping back up the curb once I passed them. Well, I almost died that day.

My determination to impress the girls overtook the part of my brain that dealt with logic and I severely miscalculated the jump. I skidded against the curb and it bucked me out to the middle of the road, into oncoming traffic. I scrambled to get back onto the pavement and my bike flew clean off the ground. I was propelled into a bush.

Goal achieved! I overtook the girls. And they did come over to help, even calling me cute when I started crying, so I took it as a win. Haven’t been on a bike since, though.


#29 Monkey Man Demonstrates Powerful Prowess 

I was 13-years-old and I had no idea how to look “cool” around girls. While riding my bike at the park, my dad called me to leave. There were a group of similarly aged girls nearby that I thought were cute. My first thought in my sub-Neanderthal brain was, “Oh, in movies they like strong guys. I can lift my bike, I’ll show off that,” as if that wasn’t the stupidest thing ever.

So I lifted my bike over my shoulder like you would a bag of ice or something, except it’s a smaller mountain bike so it’s solid metal and very heavy. I was trying to act all tough when my dad just yelled to me: “Hey bud, just wheel it, it’s just a bike.” Do I put it down and just quit it? Nah, I have a hole to dig and China is the destination.

So I just continued to walk. There I was, this scrawny, 13-year-old with a big bike on his shoulder, slowly and carefully making his way across a playground to his car. The girls didn’t notice me at all. When I got to the car, my dad just took the bike from me and said, “It wasn’t worth it, huh?” I just stayed silent. My poor father probably sat there like, “Bless his soul, he’s lost his mind.”


#30 Hopefully He Didn’t Interpret It As Stalker-y

I liked a kid in my high school who would wear the same five exact outfits every week. Every day when we were in the fourth period, I would write down in a notebook what he was wearing and what day it was. I gathered data for around two months. When I felt like I had gathered enough, I started to analyze his trends.

I found out what he wore every day of the week and matched up my outfits so it looked like we ‘unintentionally’ matched. I did this every single day. I even searched for the exact stuff he was wearing and bought the female version of it (most of it was from Target). I told him about it a year later when we were juniors because it was weighing down on me how weird that was and now we avoid each other as much as possible.


#31 Becoming Bilingual In The Name Of Love 

I learned Japanese just to impress her. I took a class, attended seminars and even bought Rosetta Stone. We have been going strong for four years now, so I guess it was all worth it. However, I don’t think learning Japanese was what really helped me impress her. I think it was just that I was wholly confident in myself and knew exactly what I wanted.


#32 Accidentally Obtained A Skydiving License 

I had a big crush on a girl who I  met on the bus going home. We talked a bit and she told me about skydiving (in Romania, it’s free for people who are 16 to 23 years old). She also told me that she had signed up already. I went to the airfield and signed up as well just to be there with her and stuff. But she didn’t end up attending the courses and I later found out she didn’t like me. Right now, I have my skydiving license and I don’t regret a thing.


#33 Improvised Karaoke Is Perfectly Romantic 

I got up on stage and sang karaoke with modified lyrics directed at my crush. I also got three other guys to help me out, but they all told me it was a bad Idea. I should have listened. Last I heard she had gotten married, had two children and was happily doing her thing.


#34 RuneScape Girlfriend That’s Not A Gold-Digger…How Does Such A Thing Exist 

Way back in middle school, I was playing some good old RuneScape. Some girl in Lumbridge (a starter town) asked me for directions. I told her I would show her how to get where she wanted, but instead of actually walking there I teleported nearby and told her to meet me. I felt super cool because the ability to teleport to that location had a lot of requirements.

Well, she never showed up, so I added her as a friend. Didn’t see her until a week later. I don’t know how but we started talking and eventually “dating” in RuneScape despite being a whole country apart. Fast forward and we’ve been together for almost eight years. Still somewhat long distance, but we are both on the same side of the country now and usually see each other every month for at least a weekend.


#35 Not The Kindest Thing You Could’ve Done, That’s For Sure 

In elementary school, I liked this girl and I saw her touching her nose. I shouted, “EW YOU’RE PICKING YOUR NOSE!” so people could hear. Twenty years later, we’re married with two kids. As a joke, we say “Hi” sometimes when we pass each other on the street. Anyways, you’re probably wondering how calling her out on picking her nose was supposed to impress her. Well, my dumb logic was that by embarrassing her, she would think I was cooler than she was and I would be excused from anything embarrassing I’d do since she got caught picking her nose. I know, in hindsight I was just being an irrational meanie.


#36 Sometimes A Little Face-Breaking Is The Only Way To Know You’re Being An Idiot 

I borrowed one of her friend’s BMXs to ride off of a home-made ramp, about two feet high. I had never jumped off a ramp before. Unsurprisingly, I landed directly on the front wheel, bounced once or twice, and ate the pavement. I had road rash all over my face. I was 11-years-old and I still remember the shame well.


#37 Ne’er-do-well Successfully Woos Goody Two-Shoes 

I told her all the trouble I used to cause in school. I’ve been expelled eight times. Those stories come off as interesting and charming in a devilish way to some people. She was a teacher. She didn’t appreciate it. She saw right through the “fun” part and saw all the mental damages that led to my behavior. She still married me though, so I guess hooray for low standards.


#38 Just Be The Best At Something 

In seventh grade, the boys in my art class used to have competitions among themselves. They tried to find out who could drink the most distilled vinegar, who could jump down the most steps on the stairs and who could suck the ink out of these little ink cartridges. It was pretty gross. It’s weird that they thought doing those things would impress girls, but it totally worked.

I had a huge crush on the guy who drank the most vinegar, regularly ate ink cartridges and jumped down a whole flight of stairs in one go. He actually became my first ever ‘boyfriend’. Ten years later, and I still think of that little dummy fondly.


#39 Kind Of Sad, To Be Honest 

I was 15 years old and had a huge crush on this one girl who flirted with me on the bus from time to time. I finally walked up to her at the bus stop and shouted at the top of my lungs, “HOW HIGH?!” She looked at me amongst the others and said, “What?” So I repeated, “How high do I have to climb this telephone pole before you say yes to a date?” She said the top.

It didn’t end up as bad as people might expect. She stopped me before I got to the wires and said yes out of fear. I ripped my shirt. We went out on a date; to mini golf with some of her friends. I got a kiss at the end of it. Never went on another one because she ended up being rude and obnoxious. Last time I saw her, she was having a hard time getting off the illicit substances.


#40 Probably The Harshest Rejection Here 

When I was about eight-years-old we took a field trip to the Field Museum in Chicago. During our lunch break, I decided to wander off to the gift shop and see what they had. I had a huge crush on this girl named Victoria in my class and I saw this ladybug ring. I knew she liked ladybugs and I had money my parents gave me, so I decided to buy the ring and give it to her.

I was really nervous and kept waiting for the right time to do it. I eventually decided to just go for it and walked up to her near the end of the trip. She was with some of her friends which made me more nervous, but I found the courage to do it. She looked at the ring and laughed. Her friends joined her and she tossed the ring in the trash.

I was completely devastated and tried hard to hold back my tears. Even though I’m over it now, that completely screwed my confidence with girls for a long time. Looking back, I may have embarrassed her too, giving it to her in front of her friends, which is why she reacted that way, but whatever the case, it’s probably the most embarrassed I have been in my life.


#41 Taking The L Isn’t As Noble As He Thought It Would Be 

I sat next to a girl I really liked in high school calculus. She would get upset because I’d get A’s on tests and she kept getting C’s. She cared a lot about her grades so I tried to be comforting, assuring her that it was a hard class and that I just had a lot of lucky guesses. She was having none of it, so I decided to get a C on purpose on the next test. We got them back and I was all excited to show her, but she got her test back and she failed. Like, below 50%. She wasn’t impressed with my C and neither were my parents.


#42 Does My ‘Eye Damage Me’ Look Pretty? 

In high school, my crush walked up next to me while I was going through my bag. The sun was in my eyes and I had a crazy thought that lighting would make me look beautiful. He walked away after two seconds and I had a black spot in my eye for two days. Lesson learned: just be yourself and don’t overcompensate for a boy.


#43 The Supreme Dedication Required For This…Wow 

I caught a couple of buses and went to a mall which was a city away just to get her favorite cupcakes. I had to carefully calculate my trip so I could get them to her during her half-hour break at work. In order not to throw her off guard, I had told her that I had passed by the mall to grab something else and just happened to be in the area where she worked.


#44 And It Was All In Vain 

I was about nine years old and kept riding my friend’s bike past my crush’s house to get his attention. I thought it would be cool if he saw me riding her bike with no hands. Unbeknownst to me, her bike didn’t have brakes. I hit a gravel patch and got slammed to the ground because I couldn’t control the bike.

A random neighbor found me crying with my arm and face covered in road rash. I didn’t find out until school the next day that he and his family were on vacation and I was riding back and forth in front of his empty house.


#45 He Smells Terrible, But He’s Cool And That’s All That Matters 

We were walking to a park to hang out, and the girl he liked was walking with us. He wanted to impress her by jumping over a ditch that was probably four to five feet deep with runoff water. The jump was about six to seven feet. My guy got a running start but actually landed directly in the center of the ditch, completely drenching himself in runoff water.

What does he do? He swims out and acts as if nothing happens even though we’re all laughing. He continues his whole day soaked in dirty water and flirting with this girl. They eventually had a child together, so I guess it worked?