October 25, 2018 | Scott Mazza

People Share The Most Embarrassing Thing They Did To Impress A Girl

“Every moment spent on impressing others, makes one's life shorter than it already is." ― Edmond Mbiaka

“A simple compliment goes a really long way - for a guy to just come over and say, 'You have great hair' or 'I really like your dress,' and then just smile and walk away. That's a great move, because he's sort of putting himself out there by doing that, but it won't lead to any embarrassment if the girl isn't interested.” ―Stacy Keibler

We’ve all been there. That moment when we take our life into our own hands and try to impress a crush. Of course, this hardly ever goes as planned, and instead of leaving a positive impression that would drive them into our arms, the result is often complete embarrassment. Such is the pain of growing up. Don’t want to relive these past moments of embarrassment? Well, then, take a look at some of the most embarrassing things other people have done, as shared on Reddit.

 Impress A Girl facts

42. Simple Plan Backfires

When I was in fifth grade, I was on a field trip with my class. I liked this girl who was sitting behind me, so I proceeded to turn on my Walkman, throw the headphones in, and sing the entire Simple Plan CD, very much out loud. About 8 songs in, she tapped my shoulder and she told me I had a terrible singing voice and politely asked me to stop. Needless to say, I was devastated my plan backfired on me.

It still makes me cringe telling the story, but there it is.

 Impress A Girl facts

41. Clearing the Chest

I used to talk to this girl through messenger... I think I was 16 at the time. So a conversation goes this particular way of bringing up what she likes in men.

Straight off the bat she says, "no hair on chest." What do I do?

Yup, go straight out and buy waxing strips and make my mom perform the obvious procedure.

I've never sweated so much in my life the few days after, the sweat was literally dripping through my school jumper...it was the most ridiculous thing I have ever done. My mother always brings it up at the most inappropriate moments.

 Impress A Girl facts

40. Racing for Her Heart

Tried to impress a girl by beating her in a foot race. I underestimated her speed so I pulled her hair and slingshot myself ahead. I won the race but not her heart.

 Impress A Girl facts Pixabay

39. Chocolate Milk Disaster

I only told a handful of people about my story. First day of 7th grade, and I am dressed in my red adidas tracksuit. Ladies, control yourselves. My friends and I decide to chat it up in the cafeteria in the morning before class. We are talking about classes, and seeing who has the same class and all that when we see a group of girls.One girl in particular caught my attention.

To my surprise she comes over to our table with her friends. We begin talking about what classes she has and I begin to drink my chocolate milk. She continues to talk and I take a look at the bottle of chocolate milk. It says, "shake well." That's exactly what I did...little did I know that the cap was long gone. I shook the bottle and chocolate milk went all over her and myself. My awesome outfit and all over her hair. Had to go to classes smelling like chocolate milk on my first day at school.

 Impress A Girl facts Flickr, Steven Depolo

38. The Mentos Game

In the sixth grade, I had a crush on a girl in my grade. I had never really talked to her, but one day we were both at our local swim club. I saw her waiting in line for snacks at the snack bar, and a few moments later I see her with a tube of mentos. I thought to myself, maybe if I had mentos she'd be instantly attracted to me!

So I walk up to the snack bar, get myself a tube of mentos, and walk around her a million times trying to see if she'd notice that because of our snack choice we were meant to be. She didn't notice. So I grabbed life by the horns. I walked up as close to her as possible and shouted "OH MY GOD, these mentos are DELICIOUS." She didn't even notice me.

Now all my best friends (almost 10 years later) like to make comments about mentos being so delicious whenever I'm around a girl I like.

 Impress A Girl facts Pixabay

37. Failing in Every Way

I tried to pet the shark in the shark petting tank at the aquarium, and upon petting it, my sleeve went all the way in the tank, the shark pooped itself, and when removing my arm from the tank, dripped dirty fish water and runny crap from my sleeve...needless to say, I saw neither the girl, the jacket, or the shark again…

 Impress A Girl facts Pxhere

36. Nightmare on Wax

I was 17 and at a party in a garage. Lots of underage drinking was taking place. As the amount of alcohol consumed went up, common sense went down.

It is worth noting that this garage was not attached to a house and had no electricity. There were plenty of candles to keep the place lit (which is why there is a new garage in the same spot, but that is another story).

As the night continued, the guys in the room were all competing for the gals' attention. Metaphoric pissing contests began. "I can drink more than him." "I once got into a fight with a dog," etc etc. I imagine other stupid things happened, but mine eclipsed it all.

I saw my ticket to "win" this night and get all the attention my drunk self thought I deserved from the ladies. A tea candle ( you know, one of those candles that has an aluminum base to hold in the wax after it melts.). It was still lit, but all the wax had turned into a pot of molten glory.

I got everyone's attention and picked that candle up, blew out the wick, and downed it like a shot. My immediate feeling of pure hardcoreness was very quickly replaced by regret as the wax first burnt my mouth, then my gullet. The pain was excruciating, but it did not stop there. The wax, after cooling within the first stages of my digestive system, begins to solidify. I have no way of explaining this feeling other than, "what the actual heck is happening to me " so I'm going with that.

Much coughing and red-eyedness followed as I attempted to clear my mouth / gullet from this waxy death. Beer helped. Clearing my mouth so I could breathe, I must have looked like I just took a load from a waxwork model. I continued the night as if nothing had happened.

I can't remember which woman I was trying to impress, but I went home alone that night. It was all a haze of cheap beer, cheap tobacco and cheaper candle wax.

 Impress A Girl facts Pixabay

35. Alternative Methods for Attention

In elementary school I was In love with a girl in my class. I didn't dare to say a thing to her, so instead, I kicked her in the crotch with full power and without warning. That got her attention…

 Impress A Girl facts

34. What’s With the Violence?

When I was in first grade, I was playing on my school playground and jungle gym. There was this cute girl there, and as I was running across one of these little "bridges," she intercepted me.

We just stared at each other for a good 5 seconds until I broke the ice by punching her in the face and running away. I never got her number.

 Impress A Girl facts

33. All for Pity

Okay so it's the beginning of my sophomore year in college and I'm at this party. I know absolutely no one at this party but the guy I showed up with, Frank. The host being awesome, asks me to be his partner for beer pong. Never played it before. We won 8 straight games. I'm feeling pretty lit up at this point. The host leaves and switches with some other guy. Other guy and I lose the next game to a couple of Senior ladies.

They ask us what year we are and we tell them our years. They then say of course they won because they have experience. One of them seems to be checking me out and I think, "you got this bro." So I start asking her about her major. Does she like it now that she's in the core of it and going to graduate in it the next year? Turns out she's a Social Work major wanting to work for DCS. She then asks me if I know what DCS/Social Work is. Being incredibly offended by someone doubting my intellect, I not only tell her that I know what it is but that I was part of the system. Which is a total lie. I had a pretty great childhood with relevant mom and pop.

So I then start making up story after story after story to impress not realizing that I'm trying to go for the pity sex. I had burnt myself that summer working over a flat iron grill. The grease got too thick on it and it popped up on my arm, leaving a nice circular burn. I tell her that it's a cigarette burn from my foster father. Surgical scar on my arm? Yeah, that's from where my foster father went all Departed on my butt and broke my arm needing surgery to heal. I tell her my younger sister is still living with them and I'm doing what I can to get her out of there and be her legal guardian.

She's looking incredibly sympathetic at this point and I'm thinking, oh yeah, I'm in. She tells me she's going to the bathroom and she'll be right back. I go to find Frank and tell him that no matter what he hears about me, just go with it. So I go to look for her, she's on the back deck bawling her eyes out, and that's when I realized I went too far. She goes on a hour-long sobbing rant about how she wants to help me and that she wants to find me on facebook and help me get my sister out of this abusive household.

Well, I make a fake Facebook and add her. Turns out Frank's roommate had been vying for her attention for some time. Frank ratted me out to his roommate and his roommate told her. She randomly walked up to me on campus, slapped me, and told me how horrible I was.

 Impress A Girl facts

32. Hot for Teacher

Had a crush on my first grade teacher. Mrs Simmons. I found out that teachers had to buy school supplies, and her birthday was coming. I went home, cleaned out my craft box and gathered all my crayons, pens, and elastic bands, and wrapped them in lined paper for her. Got a kiss on the cheek. Never washed that cheek.


Impress A Girl factspixabay

31. You Spin Me Right Round, Baby, Right Round

On a field trip in sixth grade, I had a huge crush on this girl and I'm pretty sure she liked me too, up until I embarrassed the heck out of myself...

The park we went to on this field trip had some swings, so we were next to each other with some of our friends swinging. We did that thing on the swing sets where you twist the seat around while in it and when you let it go, you spin really fast, I don't know if anyone ever did that.

So in my 6th grade mind, I thought a good way to impress this girl was to spin the fastest, so I got my friends to twist the swing to its maximum, so much that the chain started to kink up. When they released, I started spinning too fast and ended up sliding out of the seat. As I slid out, my shorts and ankles ended up getting caught in the swing, so there I was swinging really fast upside down by my ankles with my tighty whities for all to see. I'm pretty sure my man part made an appearance as well.

My crush and everyone else laughed at me the whole time I was stuck spinning around and around and then after the swing finally came to a stop I fell out onto the ground, pulled up my pants, and ran away in a zigzag fashion, being dizzy and all. Never talked to her again…

 Impress A Girl facts

30. Can I Kick It?

I was 8, just learning how to kick a soccer ball correctly. Thinking that I'm hot stuff, I brought my ball outside and started talking to the neighbor girl about how I could kick it so high and far with no problem. She believed me and wanted to see it for herself. So I tell her that I can easily kick it over her house. Only one storey with an inclined driveway, I decide to line up my kick on the street. I get in the zone and just kick the everloving heck out of this ball....right through her front window. Not even close, I booked.

 Impress A Girl facts Stocksnap

29. The Bribe That Didn’t Work

In first grade, I gave my crush one of mom's necklaces and a couple of dollars in hopes that she would like me back. It didn't work.

 Impress A Girl facts

28. A Load of Nonesense

I was chatting to a sexy older woman at a party(me 18, her mid 30s), laughing and joking along with each other and talking about something (I don't remember what) that was fairly intellectual, and I felt like I was holding my own and she was impressed. Fast forward maybe 20 minutes, and I have been drinking too quickly, the music has gotten louder, and I have no idea what she is talking about.

She says something to me that sounds like a question but I have no idea, this stupid, STUPID part of me thinks, "Aah everyone is drunk and the music is loud, we are just chatting crap and it doesn't matter what I say!" I just spit out a sentence of little or no meaning, with a few of the words she used in the previous sentence thrown in, in a really loud voice, right in her ear.

Her face completely drops, to her it sounds like I've just been taking the piss, probably the whole time, and now I am doing an impression of her right back in her face. She just walks away without another word and I feel terrible, I go outside and sit on a step, hoping she doesn't tell anyone what a jerk I am, until my dad wants to go home, yes, my dad.

Impress A Girl facts

27. Curb Vomit

I'm a girl. I tried to impress a new boyfriend by challenging him to a drinking contest. Downed 3 pints of Guinness way quicker than him, he was really impressed...Until we got outside and I projectile vomited all the way across the street, I mean literally from one side to the other. It was a violent green colour.

 Impress A Girl facts Stocksnap

26. From Vietnam to Prom

In my high school, it was a thing to ask your date to prom/homecoming/other dances in creative ways. My girlfriend at the time was a band person...so in the middle of her band class, I burst in and rapped an invitation to prom. The best I could come up with was to rhyme prom with "Vietnam."

There were videos taken. I hate my life.

Sorry, I left out a fairly important detail. I was an 18 year old, gangly Indian boy. Ugh.

 Impress A Girl facts

25. Machine Messages

When I was a teenager, I called the home phone of a girl I had a big crush on, she didn't answer so I sang "I Want You (She's So Heavy)" by The Beatles on her answering machine.

She called me an hour later to tell me what a tool I was, but apparently her parents got a big kick out of it.

 Impress A Girl facts pixabay

24. Winded

Grade 10. Half day at school, and me and some friends decided to go to the park nearby. We were playing sandman/grounders on the swing set, and my crush was 'it.' We were having fun because it was taking her a long time to catch someone. In the end, I took pity and faked getting caught. Was pretty smooth about it. Now, I try to look all macho and jump from the top of the swing set. It was pretty high. Land on my butt and get the wind knocked outta me. Wasn't able to speak for a few minutes. Everybody had a great laugh. I was embarrassed as can be.

Impress A Girl facts

23. A Whole New World

I showed her my Minecraft world. It seemed like a good idea at the time, how naive I was.

 Impress A Girl facts pixabay

22. Falling Face First

I'm a girl. The most embarrassing thing someone has done to try to impress me happened when we were both around 15. He tried to jump over a fence at about waist height, but his shoe caught and he fell face first into the floor. In front of a whole McDonald's full of people.

I still went out with him.

 Impress A Girl facts

21. Power Sliding Gone Wrong

Tried to do a power slide in my car right in font of her. It was an epic fail and I hit another car in the process.

 Impress A Girl facts

20. Bad Donuts

I was driving with a girl I liked. I decided to do a doughnut in my truck. As we spun around a cop pulls up. I got a ticket for careless driving.

 Impress A Girl facts Pixabay

19. Experimental Dance Moves

This isn't hugely embarrassing, but it's one of those stupid things that my brain won't let me forget: I was at a club dancing drunkenly and noticed two girls nearby looking my way. Instead of just continuing to dance, or going over to them, I for some reason decided to try some little spiffy dance move that sort of involved raising my hands and doing something with my feet, that felt as stupid as it surely looked. The girls laughed at me and moved away. I still to this day don't know what look or style I was trying to pull off, or why.

 Impress A Girl facts pixabay

18. Grand Entrance Wipeout

I had a huge crush on this girl. Her best friend was having a pool party one summer during high school. I wanted to make a grand entrance, so before she saw me I intended to run from inside the house to cannonball into the pool outside. I started running and stepped outside, only to wipe out spectacularly on the side of the pool and fell halfway in. The whole party turned to me and laughed, including the crush. This was even before I started drinking.

 Impress A Girl facts Pxhere

17. The Butterfly Effect

I brought my girlfriend to Niagara Falls, since she had never been. She loves animals and insects, so I knew she would love the butterfly conservatory. Unfortunately, I have some kind of phobia or something and I was very tense around them, but tried to hide it so she could enjoy herself. We were walking around, moving, and they weren't landing on me, so I thought all would be well.

She then sits down on a bench to admire how beautiful it all was. I sit beside her. Since I wasn't moving around, the things kept getting closer and closer. Eventually at around the 5 minute mark, she looks behind me and smiles, I turn to look and there is a HUGE and I mean HUGE butterfly about an inch from my face. I scream and grab her, everyone looks at me, and she is dying of laughter. After that, we left. I felt bad I ruined it for her, but she said she had a good time. It's bad enough that it happened, but she told her girlfriends, parents, etc. It did make a good story though.

 Impress A Girl facts pixabay

16. Bursting His Bubble

I once gave this girl I had a crush on a big, red, heart-shaped balloon. She took a hairpin out of her hair and burst it, right in front of me.

 Impress A Girl facts pixabay

15. No Good Excuse

When I was 18, I went to a friend's house party and got very, very, very drunk. I knew I was past the point of no return so excused myself for a quick tactical chunder. Earlier in the night, I had been talking to this cute girl for a while, we were flirting casually and seemed to have hit it off. Fast forward to myself puking up half a bottle of Jagermeister, and who should be at the front of the bathroom queue but miss cute girl herself. It's a little hard to be sick quietly, so after hearing the wet sounds of vomit hitting water, she asked if I was being sick.

"No! I was just going for a poo."

She didn't use the bathroom, nor did she flirt with me anymore that night.

 Impress A Girl facts

14. Thanks, Mom

When I was in year 5, I stupidly told my mom I liked a girl at school. She went out and bought flowers and chocolates for me to bring into school, which I did. Unfortunately, that day I was late, so I had to give her the gifts in front of my whole class, which involved a lot of laughing from them, and a rather large red face from myself. I went over, gave her a large bunch of flowers that were nearly as big as me and the box of chocolates. She looked embarrassed and pissed, so it didn't work. I heard she kept the chocolates in her desk for months until they went moldy. I love chocolate as well.

 Impress A Girl facts Pixabay

13. Showing off on the Mountain Bike

I may have overstated my mountain biking prowess.

I agreed to go with a young lady and her roommate on a fairly long trek. (Although I had owned my bike for 5 years, it probably had in the neighborhood of 5 miles logged on it.) The first street we crossed, I timed it poorly and picked the front wheel up too soon to pop over the curb. It came down right in front of the curb, and I flew over the handlebars.

The ladies were very concerned, but I assured them that I was alright, just not paying attention, etc. and that we should continue. By the time we hit mile 12 or so, I had come off the bike several times, always offering up a valid excuse as to why it wasn't my fault. It wasn't really that I couldn't ride a bike, so much as I was trying to keep up with them, and couldn't do it safely.

Then the last wreck was a doozie. My head hit the curb and blood was everywhere. Fortunately, we were about a block from the hospital, which I later found out the ladies had planned. They decided around mile 3 to head that direction, as they could tell the bike ride was not going to end well. Anyhow, I received 17 stitches from that last incident, right in my eyebrow. Additionally, I received 9 stitches from the FIRST wreck, and 7 stitches from wreck 3 or 4, I forget which, they were all running together by then.

 Impress A Girl facts pixabay

12. Karate Kicks

I was in karate from ages 10-12 or so and had some decent skills. My sisters were in dance class at a community center and instead of taking the taxi home, a girl I really liked offered to drive us home. When we get to the house, she comes in for a minute and I want to show her how I can kick over my littlest sister's head (which I'd done a million times before).

I kick up, perfectly high enough...but do not sweep over enough for my foot to be on the other side of my sister's head, so it comes down and drops on the top of her head like a hammer and I almost fall over.

I never did get a date with that girl.

 Impress A Girl facts pixabay

11. Taking the Wrong Dare

Accepted a dare to run around my friend's house naked. It was...cold out.

 Impress A Girl facts pixabay

10. Falling Into Addiction

When I was 17, I started doing drugs. All to get with a girl. I knew she would be interested in trying the harder stuff, and she would be even more impressed that I had the hookup. So one night, I got some stuff and asked her if she wanted to party.

It worked, I wasn't wrong about her. What followed was over a year of slow falling into full-on addiction and all the fun that brings with it. We had no trust in each other, nothing in common outside of our love of drugs. She had money, I had a connection.

I started failing my college classes, driving 400 mile round trips every weekend to hang out with her and use. Not one of the best moments or periods in my life.

There is a silver lining. As I descended into the pit of addiction, borrowing money and selling all my stuff, I became closer with a good high school friend and coworker at the restaurant I cooked at.

She gave me an opening. I took it. Clawed my way out of the friend zone, ditched the addict girlfriend, quit doing drugs the day I got with my future wife, and have never touched the stuff again.

Looking back, it was all so stupid, but childhood crushes don't die easy. It took an addiction and one very special woman for me to move on. I would have never quit without her, and wouldn't ever be able to stay clean without having her to lose.

Impress A Girl facts

9. Skate Park Fail

Biking around a nearby town with a good buddy. An MSN Messenger status had revealed my crush would be going to the town's dinky little skate park. I'm awful at biking and skate boarding and such but I want to impress her.

We get there, she's not there yet. So I decided to take a practice run up one of the ramps. Turns out it rained the night before, so right when I got to the top, my bike slips, I wipe out and slide all the way to the bottom to see my crush just arriving at the park. I'm bleeding profusely, start crying, and have to wait in awkward silence until my mom picks me up.

 Impress A Girl facts pixabay

8. Row, Row, Row Your Boat

I was at the gym in school with my huge rugby friends. They were taking turns at seeing who could row 2000m the quickest. There were a few girls watching the spectacle from the side, and my father used to row for his university so I decided I, too, would join the fray.

Now, I am a finely tuned athletic machine, however, I am also five foot tall. Thus, I was forced to row like a machine to make up for my short arms. Fortunately, the threat of looking like an idiot kept me pulling my way through to a respectable time. The only thing was, I was screwed. The rest hadn't been working too hard and were comparatively fresh. The most experienced member of our group asked if anyone wanted to do another round. The rest declined, but, to impress the girls, I committed myself to another 7-10 minutes of awfulness. I could barely walk afterwards, and fell up/down every time I encountered a stairway.

 Impress A Girl facts

7. Nervous Backflips

In 3rd grade, I would always run to the swings at the beginning of recess. I would get on the swing for 2 minutes before the girl I liked would come over and ask to get on it. So I would pump as high as I could, grab the chains, and do a backflip off the swing! I looked like a total tough guy! Then I would run away because I was too nervous to actually talk to her...this happened every single day. Even worse, she already told me she liked me.

 Impress A Girl facts

6. String Theory Incident

She was sitting next to me in class. I knew she liked smart guys. I wasn't paying attention. Raised my hand immediately after hearing the professor ask a question. (Didn't hear the question). Spent 10 mins trying to explain how I understood string theory. I don't know anything about string theory.

 Impress A Girl facts

5. A Pissy Impression

I don't remember this, but apparently when I was in pre-school, I pulled my pants down and peed in front of the neighbor boy to impress him in my driveway. My flirting skills have since improved.

 Impress A Girl facts

4. Ugly Setup

First day of kindergarten class. Love at first sight kind of thing. Her name was Jessica. I thought I would impress her by professing my love for her in front of everyone in class.

What I was going to say was, "Hey does anyone in this class think Jessica is ugly, because I think she is gorgeous."

Unfortunately, all I got to say was, "Hey does anyone in this class think Jessica is ugly" before I was immediately interrupted by the teacher. Teacher thought I was trying to be mean to Jessica by calling her ugly. I was sent to the principle's office, and needless to say Jessica never spoke to me.

Impress A Girl facts

3. Diving Right in

Me, 15-16, gets invited from a mutual friend to a pool party. See old friends, make new acquaintances, and there she is. The girl I had a major crush on. She smiles and waves and continues floating around on her back.

Attempt to dive over her, like a boss, and end up kneeing her right in the nose. There's blood, screaming, and a hundred seething fingers pointed right at my feels. She ran away crying, and I never spoke to her again.

I ended up seeing her about a week later, it was bad. I still feel terrible.

Impress A Girl facts

2. Fart Failure

Twelve years old, hanging out at my friend's for the night. His sister also had a girlfriend spending the night. They were hanging in the sister's bedroom and we were playing video games in the den. I thought it would be funny to crack the bedroom door and moon them. Their backs were turned from the door, and after 10 seconds or so with them not noticing I thought it'd be funny to rip a fart to get their attention. Bending over in the middle of the doorway, pushed one out. Pooping.

Impress A Girl facts

1. Pokemon Undies

I let my pants fall down to show what a tough guy I was and that I didn't live by the norms society set for us. I was in second grade and immediately felt embarrassed, having forgotten that I was wearing my Pokemon briefs.

Impress A Girl facts


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