35 Awkward Memories That Keep People Up at Night

‘Hasta la vista, baby’
35 Awkward Memories That Keep People Up at Night

Few memories haunt a guy like the time he almost had sex. One Redditor still remembers the time he was alone with a girl, and when she complimented his eyes and put her hand on his thigh, he froze. When he finally thought of something to say, it was “You’re a butterface.” He went on to note that the girl was not, in fact, a butterface, and that she didn’t know what the term meant, so he had to explain it to her. 

In what was likely a bout of karmic retribution, he admits that he remained a virgin for six years after that fateful night. 

This, sadly, isn’t the most horrifyingly awkward memory that stays at the forefront of Redditors’ minds. There’s also something that I’ve chosen to dub The Finger Incident.

wishmynamewasbetter 7y ago I met my celebrity crush and had the chance to have a full on, twenty minute conversation with the guy. I used that 20 minutes to be a cringy fangirl, instead of, ya know, having a genuine conversation. To this day I'm embarrassed, but I can't really blame myself too much. + 100 ...
ivorella 7y ago Edited 7y ago When I was in elementary school (probably grade 2?) the school said we could wear our Halloween *costumes to school. But apparently they changed their mind and called all the parents. Well, my family never got the memo and I showed up as a fucking fairy princess. Only person in costume. FML. Luckily I didnt live too far from school and they let me walk home and change, and then come back. + 173 ...
gaydotaer 7y ago 0 The time I pointed to my new boss's belly and said congratulations! with a huge smile on my face. Turned out she was fat, not pregnant. + 282 ...
noxiro 7y ago e Edited 7y ago I was taking a dump at work and forgot to lock the bathroom door and the CEO of the company walks in while I'm wiping my ass checking if there's any more brown stuff on the toilet paper. To make it worse I made eye contact with him and said sorry I guess I forgot to lock the door. Не just looked at me with disgust and closed the door without saying anything. + 342 ...
 7y ago I was 13. I was teaching my 50 year old large breasted full-bodied home-ec teacher to play chess. I kept staring at her cleavage while talking to her. In my defense I had recently read that it is normal for men to look at women's breasts. Clearly I mistook looking for staring. I thought it was normal at the time but looking back I remember her trying to get me to look at her face instead of what I was obviously concentrated on. I makes me cringe 9 years later. I hope I never see that woman
Zer01nfinity 6y ago . Yelling in a library when I played shooting games back when I was a kid. It was a small library and everybody could hear me when I was yelling things like Shit... Crap ... Die. The librarian came over to tell me to be quiet but still remember everyone staring at me. Still burns man + 1K ...
walrusman7777777 6y ago I was still inexperienced with my GF at the time and thought it would be spontaneous and hot to pick her up off the bed and kiss her with her legs wrapped me standing up. However, she had no idea I was intending to do this so I struggled to lift her dead weight for a few agonising seconds. Then I thought fuck this and used all my strength to lift her up but I overdid it causing her to hit her head on the ceiling light, I drop her out of shock and she hits her
StephCurryMustard 6y ago When I was a teenager I had a little crush on one of my female friends. One day she starts hitting on me and suggestively nibbles and sucks on my finger. I get all nervous and jokingly say Hey you don't know where that finger's been! I wake up some nights in a cold sweat remembering the look on her face at that moment. + 996 ...
KyogreRJ 6 5y ago Edited 5y ago e I was in school talking about music genres with a female classmate, and i was talking about what dubstep sounds like and asked the girl's number to show her some cool dubstep music, then i realised what i have asked + 276 ...
 7y ago the time I worked in retail, and I was looking for an empty dressing room to put a customer in. I walked up to the door, knock on it, no answer. so, I unlock the door and open it to reveal a man with his pants half way down, clearly he is trying them on and I've just interrupted him. we both just stare at each other for a second and I say, they look great! and I abruptly closed the door. + 2.4K ...
loveadumb 7y ago I went to an audition for a renaissance fair. I didn't even want to but my mom pressured me. She told me that you had to be in costume. The audition was at a country club. I showed up in full fucking cheap costume and couldn't find the audition. I walked around the entire country club looking for the audition literally with people laughing at me. I got there and they were trying so hard not to laugh at me. They told me to fill out some paper in the other room and the guy gave me
 7y ago в In second grade during bathroom break, i i had to go pee but all the stalls were shut. So i looked inside the crack of a stall and this popular girl in my class was on the toilet. And i said hi and when she came out the stall she told me that i can't just look at her while she's using the bathroom. Now that i reflect on that, i was creepy af. + 1.8K ...
jayhow90 7y ago . Edited 7y ago At the age of 7 I went to kiss my 4 year old sister goodnight and tried to give her a French kiss by putting my tongue into her mouth (I had seen it on TV). Dad pulled me away and my sister cried. We have not mentioned it. EVER. Edit: for those asking I am a gay male + 1.5K ...
savannahwithnoh 7y ago Edited 7y ago I made the mistake in middle school to wear white jeans to school. Everyone of my friends kept laughing and whispering behind my back the entire day. It wasn't until my last class a girl I sat with was kind enough to tell me I had period blood on my pants, and gave me her hoodie to tie around my waist. I had given presentations in 3 classes that day so everyone in my classes knew I was on my period. Luckily it was a lighter flow day and it wasn't like a murder
mit-mit 7y ago The day I asked my Mum and Dad for a 'vibrator' for my 12th birthday. I...I thought that's what those cuddly toys that zoomed around when you pulled the string were called. + 949 ...
trixy_treat 7y ago When I was 15 I was trying to get a weekend job in a pet store, the owner asked me if I was flexible, my reply was yes, of course, I've done yoga for years It's been 13 years and I still think about it, my brains way of embarrassing me at random moments 'hey, remember that time you were a total idiot?!' .... .... + 2.9K ...
Youfokinwatm8 7y ago . Edited 7y ago So I was at Noah's Ark in WI and at the time was in contact with my dad. At the time he was bald, but he had hair prior. I wasn't used to this change and accidentally walked up to a complete stranger (also bald) slapped him full force on the head, then kissed it better. (I was like 5 at the time) I look to the right and see my dad waving at me from three chairs down. The guys face still haunts me to this day.
sketchmcarthur 7y ago I was like 6 and in this real fancy hotel playing with some other kids my age, including this one girl that was really cute and I had one of those kid crushes, you know the ones. When it was time to go my parents called me over and instead of saying goodbye to the girl like a normal human being I grabbed her by the waist and whispered in her ear hasta la vista baby and ran to my parents. + 2.3K ...
deviety 7y ago Kindergarten, winter time. Come in from recess, take off toque, mitts, coat, snow boots, snow pants, pants... It's my very first school memory. And plays in full HD, with surround sound. + 2.7K ...
quiet400 7y ago I was either in first or second grade when this happened. Anyway our p.e. teacher was testing us by making us do sit ups. We were grouped in pairs and when it was my turn my partner was holding my ankles and foot. I did it but every time I did it I would fart and it wasn't one of those silent farts. No it made sound but stupid me didn't want to stop and neither did the farts. + 2K ...
plvvsh . 5y ago My sophomore year of high school I was kinda dating this guy who pretty much didn't speak. Looking back on it, he may have had selective mutism. Anyway, I kissed him during band practice but I did it in a super cringy way and it was not expected at all. And I cut my lip on his braces. 113 ...
Rob-ThaBlob 5y ago . I was 10 and the wiiU came out around that time. So my family decided to make our Miis and when my older sister was about to finish her Mii I blurt out Amy you look like a hooker. Let's just say I did not have a fun time after saying that. 596 ...
adidas jamiev99 5y ago I was once convinced to ask out my crush in school. I was 15 (now 20) and my best friend said If you don't ask her out I'm telling her you'll like her. So I built up all of my very limited confidence, walked up to her, stuttered massively and said So, I like you and shit. As a man who's now got a lot more confidence with women, it's embarrassing when this is mentioned + 1K ...
poetry-divided . 5y ago . I had to help a few teachers for a day at school. I was asked to grab an Animal Farm book from a classroom. I got to the classroom, asked for Anna McFarnbook at least 5 times, then realising 30 minutes later that I completely misread the call. + 3K ...
Heroshade 6y ago Every now and again I go back to my very first almost sexual encounter with a girl. She's got her hand on my thigh, she's running a finger over the bulge in my pants, she just told me I have really pretty eyes. Now would probably be a pretty good time to kiss her. Nah, I decided I needed to return the compliment, but I couldn't think of anything, so I blurted out that she was a butterface. Two things: she was NOT a butterface, and she didn't know what a butterface was. She asked me. I
BumbleBamble 6y ago I was very shy growing up and had trouble carrying a conversation. Writing was a strength, though, so I decided to hand write a note to the girl I had a crush on and put it in her locker (cringe by itself). To my surprise, she came up and started talking to me the next day after school. I had imagined her most likely ignoring my letter or if anything writing back. I was so extremely flustered all I could focus on was her smile and the heat of my full-face blush. She finished what she had
shoeeens 5y ago in middle school i was scared to interrupt the teacher to use the bathroom. it got to the point where i couldn't hold it anymore so i let it loose. my pants were drenched and when class was over there was a puddle of piss in my chair. i made sure i was the last person to get up and leave. + 58 ...
Fluttermun 5y ago I married into an Italian and Greek family. Very affectionate, does the cheek kiss thing upon greeting and departing, the whole caboodle- came from a no touch home. We didn't kiss, hug, shoulder pat or touch each other in anyway shape or form, so it took me a good amount of time to get used to this type of behavior. There was a point in the summer when I was still new to the family that my FIL went in to kiss my cheek and I turned to kiss his and we accidentally brushed lips. We immediately
kingofvodka 5y ago I was really drunk once, and I got a phone call. I thought the caller ID said 'Matt', which was the name of a good friend at the time, so I yelled 'what's up you sexy motherfucker! into the phone. Turns out it wasn't Matt, it was Mark who was my boss at the time, calling to ask if I could come in that evening to cover a shift. Не was very old school, late fifties, no sense of humour. The awkward silence before he awkwardly pretended he hadn't heard it will haunt me forever. + 8.4K
yamsnz 6y ago Edited 6y ago In an attempt to be less awkward I'm trying to take more time to think before I speak. This backfired in a big way in December. ran into a cousin who I hadn't seen for a few years. Не said hello and I was trying to think of a greeting since it was just about Christmas. thought would say seasons greetings or something but then I realized that might be a bit lame. So while I'm internalizing this in my head I'm basically just staring at the guy. Who is probably thinking I don't
Japulaaa 6y ago It was my first day in high school and we were supposed to introduce ourselves through a skit, well I introduced myself like I was a WWE wrestler, complete with my own ring-entrance walk, chants that I thought were supposed to hype up my new classmates and even had a made up wrestler nickname LMAO I still wake up sweating every now and then remembering that + 2.5K ...
Denpants 6y ago . Edited 6y ago Asked my crush out, she said omg ew what the fuck and ran away. Her friends nearby looked like they had witnessed a murder. I am still haunted by this.
rlover77887 6y ago - My crush came to my house to do a high school project. It involved the Internet and while she sat next to me she tried to navigate to Google on my computer. Unfortunately, the address bar auto-filled and took her to my last Google search... page two of results for her name. Every link had been clicked. We both just sat in silence. + 5.7K ...
Infranto 6y ago . I once passed what might've been the most disgusting sounding fart of all time, in front of a 100+ person class while giving a presentation. To try to cover it up, I said well, excuse you, professor My friends still haven't let me live that one down + 4.4K ...
tfc324 7y ago I got drunk and tried to fight a Navy Seal at Zuma Beach in Orlando. Не was kind to keep a cool head and not completely dismantle me. When I picture my 22 year old self, basically pretending to be held back by my friends and the insane shit I was yelling...douche chills to the max, man. 80 ...

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