People Are Sharing The Most Embarrassing Thing They Ever Did While Trying To Impress Someone, Here Are 90 Of The Most Painful
We’ve all been there—we’ve just said or done something incredibly embarrassing, we’re blushing redder than a stop sign, and we wish we could just disappear. Failure and embarrassment are natural parts of being a human being, and how we behave when we make a (very public) mistake says a lot about who we are. But some moments are so painful, we can’t help but relive them year after year. Sharing them with strangers online can help.
One redditor sparked a very open and honest discussion on the r/AskReddit community, as folks started spilling the tea about the most embarrassing things they’ve ever said to someone they were trying to impress. Get ready for a heavy dose of secondhand embarrassment and check out their stories below!
Bored Panda wanted to find out what to do if we keep remembering our extremely embarrassing moments all the time, so we reached out to Andrea Bonior, Ph.D., the host of the mental health advice podcast 'Baggage Check' and the bestselling author of 'Detox Your Thoughts.' You'll find the advice she shared, including when to seek a therapist's help, as you read on.
#1Kissed a girl for the first time when I was 13, something prompted me to say "average" and she loathed me for the rest of the academic year. Cut to 6 years later I matched with her on bumble. We met, we sexed and she looked me dead in the eye and said "average". She is my bestfriend now.
Image credits: skam_skins
#2When my dad was a kid, he tried to impress an older lady. She had asked him what he was studying, and he confidently told her “Latin”. She seemed really impressed by this, so she asked him to speak a bit of Latin to her. He knew one word, and created a bunch of other words around it that sounded Latin-ish. She frowned and told him it was a bad thing to lie.
Her job? Latin teacher.
Image credits: inexistences
#3I did once (truthfully) tell a girl from Austria that I didn't know what the capital of Austria was - which wouldn't be too embarrassing, except that I was wearing a t-shirt which said 'Vienna Rocks" on it at the time. She thought I was joking.
Image credits: Ok-Fudge8848
Dr. Bonior told Bored Panda that in situations when someone is constantly tormented by memories when they embarrassed themselves, it's important to think about reframing the narrative.
"Did the situation teach you something? Did it make you stronger? Did it give you added understanding or empathy for other people? In general, we often over-focus on ourselves and assume that people are still thinking about something embarrassing we did when in reality they are thinking about something embarrassing they did!" she told us via email.
"So ask yourself realistically, why would this be something that other people even care about? And even if they did, how is thinking about it now helping me? You can use some techniques borrowed from meditation where you visualize the embarrassing situation as a cloud that, as you breathe slowly, dissipates, or as a leaf that gradually floats away on a stream," she advised.
#4One day I went to my boss's chamber and saw his arm in a cast. I wanted to say something sympathetic and score some brownie points but what I said was "sir, your arm is broken". He looked at me and said "I know".
Image credits: SuvenPan
#5Was on an airplane years ago with my girlfriend and her parents. My girlfriend couldn't get a seat next to me and sat directly behind me. During the flight I thought I would surprise her and reached me hand back onto her knee. Slowly I kept extending it up her thigh until I heard giggling. Looked behind through the seats and saw that my hand was on the leg of the guy next to her. He saw my face and said, "I just wanted to see how far you'd go." Of course my girlfriend was in on it and started laughing along with the rest of the row. Was so embarrassed
Image credits: Ladon1949
#6First girlfriend, 6th grade, went to the movies.
Wanted to hold her hand, terrified, wasn’t sure what to do. Started giving her a sales pitch on how awesome my hands were.
“They’re really good at holding stuff, like boxes…or jugs”
Was truly thinking of milk jugs (god knows why) but accidentally suggested I could just hold her boobs.
It’s been more than 20 years and I still think of it regularly
Image credits: PancakesandScotch
Meanwhile, the author of 'Detox Your Thoughts' noted that a good rule of thumb for when to seek professional help is to look at whether the embarrassing memories people remember get in the way of their daily life and functioning.
"For instance, if it is really disrupting your sleep a lot over time, or it's keeping you from wanting to socialize, or it's bringing down your mood so much that you can't concentrate, those are all examples of how your daily life is suffering," Dr. Bonior told Bored Panda.
"But also too, I'm a big fan of therapy just for gaining insight into a situation. There might be a problematic pattern with your thinking that needs to be explored further, even if the distress that's being caused isn't completely disruptive. Getting help could still go a long way toward improving your life."
#7Not embarrassing thing said but when I was first dating my now wife i set fire to the restaurant and some random guy at the table next to me put it out. So I bought him a drink to say thanks and spilled it on his date.
Wanted to die.
EDIT: woah. I went on the p**s and came back to my wife WhatsApping me
Image credits: DM_ME_CHARMANDERS
#8My university boyfriend invited me to meet his friends at a house party. His friends were known to be quite judgmental and historically not nice to their friends’ girlfriends.
I was so nervous on the way in the car, so my boyfriend kept telling me to just try and spend some time with a guy called Johan (the nicest one of the bunch).
As we pulled up, one of the friends came out to the car and my boyfriend said: “That’s Johan. Talk to him.”
I got out, extended my hand, and said: “Hi, I’m Johan.” There was no way to recover from that.
Image credits: Annie_Brand
#9Went to Warped Tour, they had a contest to submit a photo and the winner got to meet one of the bands.
Took a sick shot with my blackberry, submitted it in its low resolution glory and won somehow.
Honestly had no idea who the band was, but I met them, got a signed poster, shook all their hands.
Then I said “you guys were awesome, great show”.
Singer said “well, we haven’t played yet so…”
Edit: did some digging, it was Warped Tour ‘06 and the band was The Academy Is…
Image credits: PancakesandScotch
Harvard Business Review points out that embarrassment can work in your favor because it shows the people around you that you’re just like them—human. So long as we don’t make a big deal about our mess-up, things should be fine.
“You’d be surprised by how compassionate and nonjudgmental your audience is. Everyone wants a leader who shows their human side. Your humility is what will make you relatable,” Lan Nguyen Chaplin writes.
Psych Central suggests practicing self-compassion or laughing things off to work through an embarrassing moment. Other things that help are common sense approaches like apologizing and owning up to your mistake. Doing some deep breathing also helps to stay calm, in the moment.
But if you feel like you’re still obsessing over your mistake, it can help to vent to your friends or to seek a therapist’s help. They might give you a different perspective that’ll help you move forward.
#10Not me but my husband. For context we've known each other since kindergarten and started dating at 14.
I was in a very edgy emo phase at 14 (it was 2007, weren't we all) and my husband, trying to impress me, and thinking I was into the "bad boy" type lied and told me that he had gone to jail over the summer. I knew this was not true, again we'd known each other since kindergarten and he was the most well behaved and easy-going kid I knew, so I asked him why he went to jail. What his 14 year old brain came up with as a cool but not too serious reason to be in jail was that he "got too high and threw a Twinkie at an old woman while he was skateboarding, but it hit her too hard, and she fell and got knocked unconscious"
I remember him saying this with 100% sincerity as I sat there trying my hardest not to crack up because I had a crush on him and he was a big dork, but it was charming. I could see that he instantly regretted saying that, like I could visibly see it on his face as he realized how stupid that sounded but I dropped it at the time and didn't bring it back up again until years later when we were more comfortable with each other. We're 30 now and I still bring it up as a joke on occasion, our kids now also think it's hilarious.
#11Not trying to date someone, but my first job interview, i got a question that was: ‘describe yourself in 3 words.’ My a*s literally said ‘lazy’. Somehow still got the job
Image credits: DaPanda21919
#12I told everyone I knew about my plan to go on a trip to Europe. I had planned to tour different countries by train with a special visit to… Amsterdam. My intention was to visit a marijuana cafe, but in my ignorance I thought that these were all located in the red lights district. I would tell people I was going to the the red light district and they would understandably pause and ask me… why? Trying to be sly I would say something like “to do what the locals do of course,” believing that this meant smoking marijuana in a cafe…
I was actually telling everyone I knew, friends, teachers, relatives, coworkers, that I was going to cross the Atlantic so I could hire a prostitute…
The most important thing when it comes to an embarrassing situation is to come to terms with what happened. The last thing you need is for it to turn into a deep-seated sense of shame that will follow you everywhere—making you facepalm and cringe in the shower, on your commute, and when trying to sleep at night. In short, you really don’t want that.
No matter how much of a fool you think you’ve made of yourself, there are two things to remember. First of all, everyone makes mistakes. Literally everyone! Even those seemingly ‘perfect’ social media stars you follow online don’t have it all figured out. Messing up and learning from our mistakes is a universal experience, no matter someone’s background or circumstances.
#13Server trying to get a tip: I went to clear a shared dessert dish from a table of 4 - mom, dad and 2 sons. One son jokingly pointed at his mom and said "She ate most of it". I, braindead server who was/is terrible at banter, but trying to get a tip said the first reply that came to mind: "I can tell"
No idea why. Terrible reaction, as expected. No tip
Image credits: 1nd1anaCroft
#14“I’m a lion, rawr”
She patted my head and said, “good for you”
#15Went to catholic school.
Lots of Ukrainian classmates.
Had a crush on a Ukrainian girl, so I asked some Ukrainian friends what I could say to her. A pickup line maybe.
So at lunch I went to her and said (and I'm probably not spelling any of these correctly) "Di me ni hlib tper!" She laughed so I went back to my friends and asked for another.
"Ya ye dournee" she laughed a bit harder. This was good material. I went back and asked for another.
"Ya popishya moi shtaneh" she spit pop and was in hysterics.
The first was, "Give me a piece of bread!"
The second was, "I'm stupud!"
And the last was, "I pissed my pants!"
Those a******s got me a couple dates with her tho!
Secondly, well, not to sound too critical, but the world doesn’t revolve around you, nor us. What might have been the embarrassment of a lifetime for us may have simply been a witty moment for someone else… if they noticed it in the first place. Odds are that everyone’s far too obsessed with thinking about how others perceive them to nitpick our mistakes.
Do people judge others? Yes, obviously, all the time. However, they probably don’t hold your mistakes against you as much as you punish yourself by going over the same memories over and over and over again. We are, usually, our own harshest critics.
#16Crush in HS worked at an ice cream store. When she asked for toppings I said “I’ll have Reese’s penises please”. The store laughed.
Image credits: WhaleyWino235
#17I once attempted to impress someone with my extensive knowledge of ancient civilizations, but accidentally referred to the Aztecs as the 'Avocados.'
Image credits: Creative-Ad5487
#18Your eyes are like Mushroom.
She laughed so hard that we dated for 7 years.
Image credits: rcorum
#19I had a crush on the receptionist of my college’s gym. One night when I was the last one in there, I got nervous making small talk and offered to help her clean up before she closed the gym, and I immediately thought to myself “wow you sound like a f*****g serial killer”
She actually got the vacuum out for me and proceeded to talk about her boyfriend. At the end of the day, not mad since I did something nice for someone lol
Image credits: PhoenixSidePeen
#20I told a musician I like that I liked a specific song. It was not his song.
Image credits: Naca-7
#21Was wrestling with a friend and we fell on and broke a Foosball table. My crush walked in the room and I said with a stupid smile, “I did that s**t.” She left without a word.
Image credits: BurghFinsFan
#22"if you had brains in your cheeks, you'd be smarter"
It was a compliment, in my head
Image credits: Smegma_Surfer
#23While on a semi date, said I was presbyterian when asked if I ate fish. He looked confused. I meant to say pescatarian.
#24Trying to lie about my age.
Her: _"You're too young, how old are you?"_
Me: _"I..eh um..I'm like 20 or 21 I am."_
As the Sentence left my mouth I realised how ridiculous I had just sounded.
**For clarification, I was 17 and absolutely hammered at the time.**
Image credits: Sonnyboy1990
#25I was around 15, going through the receiving line at my cousin's wedding. This was my first "grown up" wedding and I wanted to act it. As I hugged my cousin I blurted out "I'm so excited to be here! The last wedding I was at was your first one!"
That has echoed in my head for 30 years.
E: This was my cousin's second wedding. The groom's first.
Image credits: LGBecca
#26I worked at the local guitar shop in town in highschool. It happens to be tom Morello's home town (of rage against the machine fame). The owner used to babysit him when tom was little and he'd always stop by to say hi when they were in town on tour. This was around the time of evil empire and they were at peak popularity. He came in one day while I was there and asked if John was in. 16 year old me just looked at him and asked "do you know who you are?!?!" He just laughed and said yes. Humiliated I went and got the owner and then tried to hide and die from shame.
Image credits: matthewmichael
#27When I was a kid at tennis camp I was sat next to the new girl when I heard this weird scream from the upper tennis court. I tried to make her laugh by saying "that sounds like a dinosaur". All she said back was "that's my mother"
#28Had a friend I was infatuated with. I used to correct her for every grammatical mistake she made in her English (both of us are non-native English speakers). I was young and socially awkward and never realised how opposite the effect of it really was.
Image credits: GleeAspirant
#29“You’ve got beautiful eyes”
“Thank you - I grew them myself”
It was this cute guy working at the bank trying to help me with my account. I heard this somewhere and for some reason this was the only thing I could think of because I was incredibly shy back then, especially when it came to any male attention.
I still remember his face dropping ???♀️
#30I once called my potential interest “sturdy” and he was so offended. I tried walked it back by talking up how strong he was and how I could run full speed into him and he would budge.
We’ve been together for almost 7 years now - he’s used to my stupid compliments and just smiles and pats my head in reassurance.
#31I tried to sound like a computer hacker to impress some chick in college and told her I knew to hack Webcam. Her facial expression let me know immediately that I done goofed
#32I tried to impress the popular girl in class with my sick nerdiness because she said she liked Spider-Man so I spammed my favourite Spider-Men then asked if she wanted to walk home after school. As we walked home I was swarmed with other peers who made fun of said nerdiness, much more painfully because they found out I, the fat nerdy kid, had a crush on said girl. Still to this day I'm embarrassed mostly at myself for not standing up for myself. Mostly angry. I towered over all of them but did nothing to end the barrage. I just walked away.
#33Coincidentally met the parents of a girl I was crushing on when I was manning a stall at a trade fare and when they introduced themselves I was so autopilot at that point I said “oh so you know Jane too”.
The dad just looked at me and said “only for the last 32 years”.
I felt like such a dunce afterwards and clearly that story circulated back to the girl because she went cold on me as a result.
Didn’t get any smoother for a while either. Went on a date and she was saying something and I said “those who can’t do, teach”.
Her profession? Teacher.
No second date.
#34I manscaped for you (in front of my whole HS Spanish class)
Image credits: BalinAmmitai
#35Didn't say anything embarrassing but I liked this Mexican girl in 9th grade and I wanted to ask her out in Spanish. So I had a friend teach me what to say. Which was nice and romantic of me but the time in which the courage finally hit was the embarrassing part.
I hyped myself for an hour and finally decided to ask her during a silent reading time in class. Not sure why that was when I thought I'd do it. Just walked up to her desk and asked her and she just kinda awkwardly giggled and everyone was staring at me wondering how the f**k I knew Spanish. Courage depleted and I walked back to my desk.
We ended up sort of going out for a few days but the only way we communicated was through google translate on our phones. It was pretty f*****g stupid but a lot of highschool relationships are.
Image credits: camm44
#36I didn't say anything. When I get nervous, I tend to burp a tiny bit uncontrollably.
I burped in my manager's face.
Image credits: throwitawaybongybong
#37Was sat round a camp fire at a festival with a few friends and some random women that had joined us. Everyone was drinking, talking and having a good time.
One of the women got up and said to her friends "I'm gonna go and grab something from the tent, you coming?".
One friend replied "nah, I'm gonna stay here and get f****d".
My drunken stupid a**e took it wrong and blurted out "I'll f**k ya".
She looks a bit shocked and goes "that's not really what I meant but thanks I guess".
She meant get f****d up on booze and I still cringe about it almost 30 years later.
Image credits: Murphyitsnotyou
#38I was getting to know a girl once. She said “I’m a librarian”. I said “I’m a Capricorn”.
Image credits: Radiants_Table
#39I can do a Kickflip, then proceed to elegantly snap my ankle
Image credits: Mrlightyboy
#40At one meeting I tried to utter a pick-up line, but it ended up sounding like a malfunctioning robot: "Do you have Wi-Fi? Because I feel a strong connection!
Image credits: Imaginary-Eye1569
#41Not exactly in high school , but at the time I was in high school.
One day when I was taking the train , I met a girl from my previous high school that I haven't seen for many years and I remembered her being ugly and when I met her again she was looking absolutely gorgeous.
So we chatted abit and then I said: "You became so beautiful wow.." and then she said: "I became beautiful? you mean to say I was ugly back then? f**k off.." and I remember walking from there feeling shameful and I cringe everytime I recall this lol.
#42"I'm crushing on you so hard I think it could be considered abuse". Then surprised pikachu face'd when she didn't think it was charming. Man, 19 years old me was criiiiiiiiiiinge.
#43My brother was once having a phone interview and at the end of the call he said “Ok bye, love you”.
You should have seen his face ?️??️. Priceless.
#44Not me, my husband.
In the beginning of our relationship he was soo bad at complimenting but he felt the need to do it anyway.
So once when we traveled by bus together he just kept staring at me with loving eyes and said
'You are so different than anyone I ever meet... you... you.. i think... you degenerate from society.'
I said 'Oh, wow! NOW I feel so special.'
His face went white and started to stutter but I laughed it off.
Some times later we were at a bus stop full of people and he blurted out loud.
'Your hair is so pretty! How did you do it? Like did you wash it or what?'
'Yeah, I never do that before but I like to shake things up sometimes.'
He got a cold and a running nose, but he never had any handkerchief at hand. I thought out some romantic gesture (i was 17 at the time) I brought some tissue paper with me, but on one, I write a loving note to him.
He saw the note... Read the note... and blew his nose in it. -.-
I gave up on romantic then.
He is my husband, best friend for many years now and the father of my children. ??
#45When I was 15. I went to a Mormon dance (I’m atheist, my friend was mormon and invited me). A girl walked up to me and invited me to dance.
Apparently blood flow to my hands wasn’t effective because she goes “Ooo your hands are cold.”
I said without hesitation trying to be smooth.
“Cold hands, warm heart.”
My friend and I hit 40 last year. He still reminds me of it from time to time. I twitch when my brain thinks of it from time to time.
I’m twitching now.
edit: I’ve been in two very long term relationships since (10 years+5 years). I became way more suave out of high school. I can use sub par lines like this ironically nowadays.
Huge difference between a 15 year old in the 90s embarrassing himself…and joking about it now at 40 with my partner!
#46"Hey everyone, check this out!"
Trying to attract the attention of a beautiful girl who sang soprano in the choral program at music camp. I was a gangly violinist. We were tossing a Frisbee around.
I'd been practicing the classic, "under-the-leg" Frisbee throw. It was time to reveal my move.
A dozen campers, including my crush, looked directly at me.
I lifted my leg, flung the bee, caught it on my right pinky. It shot like a flying blade of plastic sideways and proceeded to hit my crush directly in the THROAT.
She collapsed, gasping.
She couldn't sing for the rest of the camp season.
This is the last memory I will experience as the wave of DMT floods my brain with the soft light of death.
#47It wasn’t me, but a very loud phone conversation that was almost impossible not to listen in on the LRT ride home. A guy is trying to impress a woman on the other line by acting tough, saying if some other guy does anything out of line, he’ll “bruschetta him really good”.
Like, you’ll invite him over for appetizers?
You can tell the woman isn’t getting it either because he keeps on trying to explain it to her, and he’s getting more and more agitated. He has a bruschetta at home, he’s ready to go at any time.
Finally it gets to the point that he realizes she doesn’t know what he means by bruschetta and he explains it’s a knife that they use to cut through underbrush in the rainforest.
He means machete.
At this point I lose it laughing and dude looked like he was both ready to throw down and was dying a little inside.
It’s been probably 12 years and I still think about this often.
#48Said to me, with full confidence and eye contact whilst they were holding a guitar, "I'm going to marinate you now"
I was, eventually when we both stopped laughing, serenaded.
#49Thou titties art magnifico
Image credits: DemRepInd
#50i was four and didn’t know what cooties were, but i heard it from a cartoon character i had a crush on so i thought it would make me seem cool or something?
“oops i forgot to put my cooties on today”
*walks out of room*
*enters bathroom and starts pretending to apply moisturiser*
*walks back into room* ?
#51She said she was going to the botanical garden over the weekend, so I told her about the time when I was 3 and got kicked out for eating the plants there.
#52I went for a job interview at a bank. Was waiting for my interview and a lady came out into the reception, looked at me and said "Is your name Poe-one?". I looked at her and in an almost pirate like voice said "that it be".
#53Looking at old photos of her I didn't recognise....
"Who's that fat chick?"
#54I was totally in love with this girl and got her to go to Disneyland with my friends and I, all the way from another state. On the second ride, I said "you know, Disneyland has the second most diverse amount of foliage of anywhere in the United States."
...It was true, but... why?
"What happened? Did you look in the mirror?" The next morning.
I have no idea why I said that but I did and I'm generally not a bad dude.
#56Dating my now fiance for a few weeks, we go away for a weekend
Me: ask my anything, I'll prove I pay attention to everything you've said or done
Her: what tattoo have I got on my back?
Me: a flower? It's got a green stalk
Her: its a lizard
Me: to be fair, I've not seen it much, you're always on your back
#57Me: So, where are you from?
Me: Sweet. North or South?
(My dumbass at the time knew there were two Koreas, but didn't know we won't meet anyone from the North ?. Years later I actually met someone from North Korea, and refused to believe him for a while thinking he was messing with me ?)
#58In middle school a girl called me to play with her under one of those huge half-buried tires. I went under there and she pinned me, then kissed me. She backed up and said 'That was awesome' and I responded 'Not really, I kiss a lot of girls' trying to sound cool/mature.
She just stormed off and never spoke to me again.
#59A woman was telling me about her modeling and acting stuff and simultaneously her nursing stuff. Now she spoke about a Burns Theatre which was always stifingly hot. I joked about it being well named as Burns Theatre.
.....she was talking about her nursing at that current time. I just made a joke about burn victims. Who were mostly kids. We did not hit it off.
#60Mildly embarrassing and funny...long time ago I was in my early 20s and meeting my boyfriend's father for the first time. I knew he had a dog with a "person name." So I walk in and the dad and dog are there, I lean down a bit toward the dog and say, "Hi, Bill." My boyfriend says, "That's Mike...Bill is my dad."
#61Was hanging out with a friend and two girls he knew but I had never met. One girl he was trying to date and the other girl was her friend.
After a long day of driving around, seeing a movie, hitting a park, etc. we end up back at the one girl's parents' house, who weren't home.
My friend and the one girl are fooling around on one couch while I watch TV with the other girl on the other couch.
I'm interested in the other girl but outright assume she has 0 interest in me so I'm not pursuing anything until she shows what I perceive as legitimate interest.
Anyway, I nod off while watching the movie but shortly after I'm abruptly woken up by someone laying down on top of me.
My first thought is that my guy friend is just f*****g with me so, before I even fully open my eyes, I throw him off of me.
Turns out it wasn't him, it was the cute girl that had been on the couch with me and I just WWE threw her off the couch and mortifyingly watched her land on and roll off the other side of the coffee table.
She immediately got up, ran out of the house and ran home. My friend and his girl look at me wide-eyed and just say "dude what the F**K?!"
My explanation? "Dude I thought it was you!"... this then makes HIS girl look at him questioningly before he replies to me with "why the F**K would you think it was me?"
**TLDR: cute girl makes a surprise move on me and I throw her halfway across the room**
#62When I was in college, another student fell passed out while walking, hit his head, and convulsed a little bit. I was a lifeguard at the time and ran over to assist.
I slid my laptop bag under his head and told a bystander to call 911 and tell them what's happening and where we are.
When the convulsions stopped I did my primary assessment. He had a pulse and was breathing but was still unresponsive. While waiting he started to wake up where I did my secondary assessment and asked someone to take notes. Do you know where you are? Do you know what happened? Do you have any medical conditions? Have you taken any medications today? Etc...
Shortly after EMS pulled up and I briefed them on what happened, what I did, and the answers he gave to my questions then relinquished control of the situation to them.
An absolutely beautiful woman who was a bystander comes up to me and says "That was so impressive, where did you learn to do that?"
...this is hard for me to type but I was a little shaken by it and said "I'm a lifeguard and there is such a thing as 'duty to act' so by not assisting him I could have faced legal trouble"
This was not at all where my head was at, I was just really nervous and started rambling. Anyway I saw the super enthusiastic smile wipe right off her face and I just walked off.
I still cringe about that one.
#63"Let me take this, pregnant women should not have to carry heavy stuff." But of course she was not pregnant anymore.
#64I was at a work dinner at an Asian restaurant - I had the last dumpling on the share plate, then the brisket came out and I told my co-worker to have the last piece, she was like no you have it, and I said rather loudly, but I just ate your dumpling. My other co-workers wouldn't let that go.
#65When I was a little boy, I was already girl crazy. I remember a play date with one girl. She was the cutest little nerdling with glasses and I said "Can you take off your glasses? If I'm going to marry you, I should see what you look like without them."
Even better though: also as a young boy, my stepmom had taken my brother and I out to lunch with her girlfriend, who brought her daughter. At one point, trying to impress the little girl, I actually leaned back, stretched my arms across the booth and said "I should really start thinking about passing along the family name."
ETA: I also told a pretty caretaker at daycare that my brother and I were in a famous rock band.
#66"..so you study here ?" I said this when she was in front of her classroom.
#67While dancing at a house party with a girl, we were talking about human anatomy. The girl was telling me that in short the female form is much more beautiful then a males form, and that: "vaginas are beautiful and d***s are ugly" ...
At which point I declared:
"What, I have a pretty d**k"-
Well, the music cut, at that exact moment, and since it was being played extremely loud, when It cut the entire room heard that declaration...
Shouted I have a pretty d**k to an entire house party full of people...
#68I was laying it on to this beautiful lady at an outdoor concert . All smooth and suave, talking like I was a big shot and knew all the right people there.
So, I thought it'd be a good idea to drop the name of this semi famous lead singer from a local band I supposedly knew.. you know, to show her I was connected and all that. But the problem was, I f****d up the name entirely. And it turns out it was a relative of hers. She started asking questions…
Her eyes got wide, and she started laughing so damn hard, I thought she was gonna pee herself. I felt like my face was on fire. I knew I couldn't salvage the situation, so I just laughed it off too and admitted I had no idea what I was talkin' about. We ended up talking for a bit, and we actually had a good time. Learned my lesson, though: never try to inflate your reputation with nonsense. It can backfire real f*****g quick.
#69What I wanted to say was, "Hey! How's it going?" What I ended up saying was, "Bleeagh? *finger guns*" we stared at each other for a couple seconds before I ended up walking away.
#70I approached a girl sitting in a canteen, asked if I could join her and after some talk, I asked her if she wants to eat anything and she said yes anything of your choice.
I bought her sandwich and as we were eating and to continue the conversation I asked her name and she in very cute voice told her name.
Her and my sister’s name were same , so I told her about it and the reply I got was out of the world, she said,
*I am also like a sister to you.*
That was a K.O
#71We met a girl and went to dinner at a cafe, during the conversation a bet arose, and I said that I could eat everything on the menu of the establishment
Half an hour later I destroyed the toilet, she successfully escaped, but I won the bet.
#72Some kid I knew was trying to impress a girl on spring break in middle school and said he played ‘quarterbacker’ for the team, even tho it was incredibly obvious - for more than just the botched title - that he had never played football before.
She actually bought it for a second - i think she didn’t hear it or being a middle school girl didn’t actually know how wrong that was lol - until a little game of beach footbal happened. I’m glad he existed tho cuz then I wasn’t the least athletic person there at least.
later he pooped his pants freshmen year, as an aside. But I’ll still always know him as mr hotshot quarterbacker and I still say it like that sometimes just cuz it’s funny
#73A girl I was really into asked me what's something about me that no one else knew, and I panicked and told her about my third nipple.
#74One time I sat outside at a hipster coffee shop in Santa Cruz (Caffe Pergolesi) and pretended like I was composing music. I wrote random notes on a page and I would periodically look up with a strained look while waving my pencil like a tortured conductor, pages strewn across the table. Thank God nobody approached me that could actually read music. I can't read music.
#75"Poggers" after she took her shirt off. She laughed :) which was the original goal.
#76I was doing a stage (a trial shift) at a really good fine dining restaurant. It continuously gets recognition as the best restaurant in the country. I was nervous because at the time I didn’t have a whole lot of experience and I wanted the staff to like me. The chef owner of the restaurant came to introduce himself and shake my hand. When we shook, my wrist cracked like 4 times super loud. He looked at me in horror and immediately apologized and told me he didn’t realize he had shook so hard. I said, “oh don’t worry! I’m just really cracky”.
He looked at me in a very confused way, said ok, turned and left.
I got the job and have been working with him for years but I’ll still never live that first interaction down.
#77I was trying to impress a girl among a group of girls and a spittle from my mouth hit her in the eye. Needless to say, I left quietly leaving behind a hullabaloo
#78Not what I said but what my then-boyfriend said to me on our first date.
Little context. He was a pro swimmer, very tall and very very skinny. We're talking about 1.93m and 66-70kg.
We knew each other from classes we had together in HS but went to see a movie for the first time one on one. On our way back after a great evening he told me "you're actually not my type at all and you're so much heavier than me" and I was like "ooookay my dude, thaaanks" lmao. I actually wasnt heavier than him just much smaller lol
He meant it as a compliment cos he felt too skinny and wanted to say he liked my personality a lot but I felt extremely fat and ugly after that comment. We were together for 5 years :)
#79“You look like a girl” (like, what got into me then? Good thing he didnt mind coz he dated me for 3 years more?)
#80After we talked about movies maybe on our third date I told her "you are much prettier than Bud Spencer." The girl laughed that she had never received such a compliment before. We ended up in bed later, so it worked.
#81"You know how Baby carries a watermelon in Dirty Dancing, and then she meets Johnny at the cabin where all the staff are actually dirty dancing? Well, I feel like I'm carrying a watermelon."
I just COULD NOT stop my mouth from saying words. He loved it. I was as red as a ....well, a watermelon. I had never openly said anything like that before.
He was the actual love of my life. I stupidly let him go because I didn't realise he loved me too. I will regret it forever because now it's too late.
#82When I started dating this guy I met at Warped Tour the summer before starting college, his dad wanted to meet me because apparently it was a red flag for his son to have met a girl at a concert. I went over to his house to meet his father and when he asked what I would be majoring in I said “I will be majoring in minoring”… I turned bright red and tried to correct myself. A few minutes in and his dad busted up laughing. He thankfully instantly liked me after that and now here I am 13 years later married to the guy I met at Warped Tour.
#83I “mistakenly” sent a text to her, indirectly showing off my very vibrant and cool social life (fake). Never got a reply. Thought about sending her an “ups wrong person” follow-up, but ultimately decided to just never talk to her again.
#84Back when i was a freshman in college, I had a huge crush on someone. So I had asked a mutual friend to introduce them to me. I was a huge nerd back then and the previous night before meeting them, I did a full research on the political climate of the state they came from, how to pronounce names of politicians, etc. so that we could have something to talk about (I literally do not know why i chose that topic looking back lol)
Anyway, on that fateful day, i went to the meeting place, fully prepared to talk about politics with my crush only to realise about half an hour of talking that he had no idea about politics of their state and what i was talking about.
#85Uhhhh. Geez. I've said a lot of embarrassing s**t. I was an impressively edgy teenager back in the late 90s/early 2000s.
I think one of the stupidest things I ever did was attempt to swoon a girl into sleeping with me by writing on the spot, badly written and barely thought out poetry and then getting mad that it didn't work.
#86To a tinder date: That I've been thinking about starting to work out regularly.
What a selling point.
#87Once, I confidently declared that I had mastered the art of levitation, but immediately tripped over my own feet and fell face-first))))
#88Not impress, but I liked a girl and I said "I think I'm Dave". I was gonna say I think we've met before but it came out wrong. She looked confused and said you think you're Dave?
#89I once sneezed and farted at the same time in front of my boss. I was so embarrassed I didn't know what to say so I just walked away...
#90Wrote a drunken love letter to her and sent it to her in a Facebook message.
Sorry for being a weirdo, Jenn!