What Was Your Most Awkward" Wait, You're Serious?" Moment?

what was your most awkward hahaha oh wait you're serious moment i was at work i work in retail and me and my co-workers heard a loud boom but we didn't think anything of it five minutes later an older lady who is in the store almost every day maybe in her 50s 60s came up to me and said i just drove into your building i looked at her and right before i began to laugh out loud i realized she actually did i work in a deli and we had a new older lady start i was showing her how to display the chicken breast and she turns to me and says i'm going to have to work up to the chicken my ex used to tie me up and hit me with raw chicken breast this was so shocking and out of the blue i assumed it was a joke nope turns out she had just gotten out of an extremely abusive relationship i just thought she was grossed out by raw chicken met a guy and i told him my name he said i'll probably not remember it i have memory problems i said hannah yeah i'm bad with names too met him again two days later and i remembered his name he on the other hand didn't remember meeting me and when i realized it wasn't a joke and was told by his mother that he actually does have memory problems i felt like a butthole oh well he doesn't remember me laughing at him i was on a first date with a guy i met at work and things are going good till his phone starts ringing and he tells me to be quiet because it was his wife a man was regaling his fellow party goers with his drunken jokes he described being found as a newborn in a field after his teenage mother hid her pregnancy and gave birth at home all he knew about her was she was a waffle house waitress we sat there enthralled waiting for the punchline until we realized he'd moved from the life of the party onto the invino veritas stage of drunkenness her how do we even know that dinosaurs were called dinosaurs if they're all dead now and we've never met one in real life me hahaha that's funny her what's funny me oh honey it took me literally half an hour to even get her slightly on board with the fact that things are called things because we decided on the name not because things inherently have a name we discover i wish i was joking a co-worker mentioned that she thought milk was too rich so she poured herself a glass of water and added two of those little cups of non-dairy creamer this was almost two years ago and i still don't know what to think i work as a server in a restaurant we use little wooden trays as czech presenters and since it is an open-air restaurant we weigh down the receipts with decorative stones shiny ones like for the bottoms of fish tanks i dropped a check for an older couple and when i got back the man said you should warn people that those rocks aren't chocolates i could have broken a tooth i get a lot of older people who like to josh around with me so i definitely thought he was kidding he was not he was actually mad at me because he had tried to eat the rock and it was obviously my fault my now bf and i were on our fifth date we were out to lunch and some toddlers started throwing a screaming fit bf and i looked at each other and i said something along the lines of kids are the best aren't they which is when he said oh i've been meaning to tell you i have a daughter we have similar humor styles so i started giggling thinking he was teasing he was not this one girl asked me if 9 11 really happened on 9 11 or did the news and others say it happened on 9 11 because it sounded more legit than any other day it actually happened on 7 stroke 11 but they moved it because they thought nobody would take it seriously on wednesday a customer asked me why our produce section was so empty especially in terms of stuff like lettuce i told him that it was because of extreme weather in a spain where we source most of our stuff from he cuts off my explanation with why does it matter what's going on in spain we're in scotland when my daughter said she had been stung by a bee and it went all of the way through her it turned out she had been stung on the chest and back at the same time when i was 18 i went with my then girlfriend to las vegas to meet her parents we were in florida where she lived with her aunt and uncle i found out that her dad and mom lived in separate houses right across the street from one another for whatever reason which was strange but definitely not the strangest thing that would happen that trip her dad came over to her mom's house to meet me and i couldn't help but notice he was dressed in a suit i thought maybe he was just a fancy dresser he kept asking me questions about my family and how i felt about his daughter he seemed to like me and we went through the trip on fairly pleasant terms but nothing else happened of any note once we get back home to florida my girlfriend decides to tell me that her dad thought we were coming out to vegas to get married and he dressed up because he was planning on taking us to get married that day she had to tell him that we had no intention of getting married in vegas my uncle asked my brother if he thought my other brother who's gay bleached his butthole my brother telling me the story i kept waiting for him to start laughing or smile or anything but he just stared at me with such a straight face i was like oh you're serious i don't know dude what was i supposed to say first day on a new job my boss was discussing standard office policies he said and i'd like to point out we have an open door policy here i said oh great so if i have a problem i can come to you he said no i mean keep your office door open at all times oh worked at a pet food store a woman came in and asked where to put topical flea medicine on her kids i laughed way too hard she complained to my manager who also laughed everyone knows you need flea collars for kids parents these days out with a girl for a first date playing the get to know each other game she brings up commitment and relationships and i think no big deal she's just feeling me out well i was right and wrong she said she doesn't do friends with guys i think cool no guys friends to worry about she then says no like you are going to commit to me and be exclusive then we can work on becoming friends i try to casually laugh it off thinking this must be some sort of joke i say something along the lines of well are you asking me to be your boyfriend before i even know you that's a bit odd asking for commitment to a stranger isn't my thing her response and i'm not exaggerating yes that is exactly what i mean i don't do this whole you date me for a few weeks then decide i'm not for you and you decide to go date another girl and end it with me i'll be damned if you are even going to speak to another girl while you're my man you are either going to commit now be my boyfriend through thick and thin make your business my business and be my everything or you might as well walk out now i tried to say something about how that's dating it sucks but it's the reality of dating sometimes it works out sometimes it doesn't and she snapped back about how she's almost 30 with no kids no husband and the next guy she dates will marry her and give her children whether he wants to or not i slapped 40 down on the table for a 28 check apologized for wasting her time and walked out i couldn't believe it dated a girl for four months a few years back one day we're chilling at my house ask her if she wants to watch an episode of brian cox's documentary wonders of the universe to which she told me she doesn't believe in space she was 100 convinced that the sky was all there was and that space was a huge cover-up by the government or some crap at first i laughed then we argued and i couldn't win because i haven't been to space to prove it exists we didn't see much of each other after that my mom told me she was pregnant again i was born in 1995 my baby sister is about to turn one i really thought she was freaking with me until she showed me the five pregnancy tests my siblings are 79 89 93 and 01 had to hit each decade lol i saw a largely pregnant woman and made a stupid comment about that you can't wait to get that out of you she said eh not really the baby doesn't have a heartbeat and i'm just waiting to have the stillbirth i own a small electronics design business 30 employees a part-time intern working 20 hours a week and making about 15 an hour came to me and said i have to cut my hours back to 10 a week so i'll need for you to double my salary yeah no have a nice life part of my job is in processing new employees well we had this one new guy that just so happened to be in a wheelchair so he comes in early in the day and i help him with some paperwork then he comes back in the afternoon and says i think i got off on the wrong foot with you so thinking that he is making a self-depreciating joke to kind of address the fact that he's in a wheelchair i laugh and say ha ha good one then he just looked at me blank-faced and said what do you mean the dude really thought he had done something to make me angry earlier and was trying to apologize so i did my best to awkwardly backpedal by saying that funny you think i was mad i literally spent a week cringing every time the phone rang because i was sure i was getting called into hr meet and greet with my new police chief i'd been law enforcement for a few years in another part of the country she introduces herself and proceeds to tell us that our first goal our highest priority in every call every encounter is to make her look good i laughed out loud and then realized that she was mad dogging me my quarterly levels for the entire first year were not encouraging my friend started dating a new girl he met when he was on a gap year he came back and had been dating her for months already and they decided to keep the relationship going when they both returned home from overseas we kept joking with him about her what she looked like that she wasn't real etc and he wouldn't show us a pic eventually we wore him down and he pulled out his phone to show us a picture it was a group shot of about 30 people in the jungle behind him on the right was an ugly blonde guy and next to him was a pretty brunette girl he points at his girlfriend in the picture and i jokingly point at the blonde guy and go oh this one here and all my friends laugh to which he goes yup i look at him puzzled and my brain doesn't catch up i point a game at the guy this one here yup that's her he responds it sits in the air for a few seconds everyone else has worked it out but me frick off that's a guy i reply he just stares at me then walks off then i realize he's serious yeah it wasn't a guy it was a girl with short hair with a masculine jaw we've never spoken about this nasty misunderstanding since and i feel like the biggest douchebag although he did propose to her eventually and they're getting married next year so obviously i didn't put him off that badly don't expect an invitation to that wedding broke my arm real bad once went to urgent care the doctor there said it was a hairline fracture and didn't even need a cast so i laughed considering my hand was stuck in a downward position could barely move my fingers and the bone was visibly pressing against the skin of my arm turns out she just didn't know crap we went to an actual orthopedist and he freaked the frick out and had us in for a surgery the very next morning have not been to any urgent care since i was at a kirby steakhouse teppanyaki like benihanas and as always it was the birthday for a girl across the table she was there with her mom and probably a good friend anyway once the table realized it was her birthday and we all wished her a good day she asked me how old i thought she was if i were putting money on it i would have said 13 but i figured she'd feel good if i said i thought she was a bit older so i guess 16 she got mad and said no i'm 20 i laughed she didn't then i realized she was serious now every time my friends and i go to kobe steakhouse we bring it up i went on a date with a dude in high school and he told me that he had astral projected himself into my dreams for the past few weeks to groom me intimately for him idk man i was hanging out with a couple of friends one day we were just talking and then we ended up talking about our first time masturbating one of my friend begins his tale first thing he told us was that for the first two months after he started beating his meat he did not use his hands we thought he was joking until he gave us a dead serious look all of us immediately asked how did he get off with no hands he described that he would sit down and use his thighs to stimulate his donger until he would blow his load to this day the saying look mom no hands has a completely different meaning to me i have a friend who just stared at a playboy four hours until he came he had no idea he was supposed to touch himself frankly i'm just impressed he could get himself off by sheer willpower alone i used to teach drama camp ugg i would take suggestions from the kids on monday write a half hour play based on those suggestions that night and then they would perform it on friday i once had a parent come to see me after reading the script she asked if there was a way to do a play with no conflict in it i laughed assuming that she was making fun of the other pc soccer moms i had to deal with but she meant it she wanted us to tell a story without any obstacles or confrontations i then carefully explained to her that a story without conflicts would not be a story but just a series of occurrences man wants pizza man goes to fridge there is pizza and fridge man eats pizza theater a girl i was seeing told me she didn't believe in dinosaurs her issue with dinosaurs wasn't so much creationist's denial as much as it was a belief in a marketing scheme companies invented to sell dinosaur toys also the toy companies must have planted fossils because how else did they get there a couple weeks later i got her a dinosaur plushie she was like that's what they want i worked at a bookstore and a customer asked why the hardcover and paperback versions of the same book didn't cost the same amount i chuckled and said i guess i'll have to look into that he came back to me five minutes later and asked if i had found out yet a couple of months after i left my last job i heard that my ex-boss's wife was divorcing him he was a bit of a hard bud when i worked for him not very flexible and generally a bit mean towards me but i didn't hate him for it or anything it was part of the reason i left though i end up going for a drink with a group of my ex-colleagues and in his drunken state my ex-boss asked if i wanted to know what his ex-wife had written on the divorce papers obviously i said yes and he told me she's filed for divorce because he was unreasonable i laughed in his face as he's literally the most unreasonable man i've met the deadpan lookie return made me realize he was deadly serious felt pretty bad for that i loved my dad i just feel the need to say that ahead of time my dad lived a very hard life never learned to read worked with his hands his whole life to provide for my mom and i one time when i was about 15 we were watching jay leno and he was doing jaywalking i was talking about how funny it was that people could be that stupid i said can you believe there are really people in america who don't know how many stars are on the american flag my dad kind of chuckled and then said there are 52 right i cracked up thinking it was a joke and then i finally stopped to see the look on his face and realized he was serious i felt like an absolute jerk because i knew he was hurt but i just really never imagined he was serious i learned a pretty important lesson that day about judging people and being careful what you say that might hurt someone friend i have something i need to tell you me dude everyone already knows that you're gay friend yeah that's what i wanted to tell you how did everyone know me haha funnyman what is it that you really wanted to tell me friend that was really it i'm gay me number really stop playing what did you want to tell me friend i'm gay after my sister-in-law had her son she has a lot of trouble with her weight she was big and always saying how hard it was to have a baby never again etc etc and the weight kept piling on she must have reached nearly 18 stone about 250 lbs due to holidays work and other reasons my husband and i ended up not seeing her for quite a few months when we did all meet up again she said with the most flat tone of voice i'm going to have another baby i burst out laughing because since her son was born all she would say it's that she would never have another she never wanted any more kids no i really am she says i'll believe that when i see it says i so when are you having this baby then in three months ah oh dear my mother-in-law compounded the awkwardness by saying well didn't you notice the bump basically drawing even more attention to sill's weight i still cringe thinking about it and it was four years ago i was at work one day with a couple of other people and we had a shift manager that liked to fake fight and punch people for fun one day one of our co-workers came to work and announced that she was pregnant he thought it was a funny joke ran up to her and punched her right in the stomach she was furious hanging out in a bar in downtown nashville playing wingmen to my buddy and fending off advance is a very large drunk girl who thinks i'm more attractive because i'm married i make small talk with a tall lanky younger dude who says he's in town to play bass for some various bands we talk about life in between songs he tells me about being recently married and we talk about our wives for a few minutes after a long silence he stares off in the distance and says well time to get this ring off and find somebody to freak am i right it was at this point that i realized how drunk the kid was and i spent the next 30 minutes explaining to him that no being in a different zip code didn't count as a legitimate reason to cheat on your wife my close friend was chatting with me the day of our college graduation each with a degree in biology they thought birds weren't technically animals and had a separate category i still haven't been able to convince my fiance's family that insects are a subcategory of animal a new co-worker came up to me one day and said what comes after 999 she got offended when i laughed turned out she had a learning disability and couldn't make the cognitive leap from nine to ten a close friend of mine we've known each for six years now never once have they led me to believe they were religious so the other day i'm scrolling through my timeline on facebook and i see a post from him concerning the super bowl halftime show it's a religious post about how lady gaga is lucifer falling from heaven and how she is pure evil all y'all my theft rikers need to open your eyes and he completely agrees with it i laugh and comment back letting him know how funny he was being such a joker nope he was dead freaking serious everyone lady gaga is lucifer i was at an engagement party two weeks ago an old friend from home i haven't seen in a long time school friends i haven't seen in years was mingling a bit and spotted my old friend simon now i moved away four years ago so i decided to go up to simon and say hello it's been a long time etc walked right up extended my hand well simon man it's been ages good to see you i'm not simon what of course you are i'm not simon you're freaking with me at this stage i turn to the other two old friends standing beside us no that's not simon juncko that's paul na you're freaking with me we thought you were joking junko that's paul it turns out that in our rural area of five or six villages there are two people completely unrelated who are basically doppelgangers simon and paul i could see his face slowly start to tense up as i kept forcing the issue i was adamant this was simon and this guy gets this a lot apparently it finally clicked and the cringe flooded over me i still replay the exchange in my head weeks later and grown when i was in middle school there was a period of a few weeks when kids would fake seizures to get a laugh it was the hip thing to do so i was at the mall toy store one day and i came around the corner of an aisle and saw a kid a little younger than me on the ground absolutely killing it i delightfully shouted dude you are good i'll never forget his parents faces when i looked up and figured out what was really happening when i was in fourth grade i had a seizure just before class apparently several of my classmates thought it was funny and dropped on the floor convulsing as well everyone was laughing for a while before my teacher came in and helped me i can't remember a thing but i wish i could it sounded hilarious my girlfriend and i are freaking and mid-thrust she asks me to marry her i stop and look down at her and she is like don't stop and i mean it and that's how i got engaged mid coates your dong is worth more than a diamond ring apparently it was very well known in high school that i was gay i can't remember the details but my friend made a joke about it my table of friends and i all laughed the teacher walking by stopped and shouted matthew you can't call someone that that's disgusting we all just stared at her and you could see in her face a slow realization she never apologized on my 25th birthday my newish boyfriend told me he was going to surprise me and do something special as a birthday dinner he told me to get dressed up and wait for him around 7. i was super excited to wear a dress for once got all dolled up and was eagerly waiting for him when he showed up he was wearing jeans and a t-shirt and just holding a grocery bag with store-bought sushi i laughed thinking this must be a precursor to the actual big night out nope we just ate store bought sushi in my living room it was actually a pretty nice time but he shouldn't have hyped it up so much my ex spent literally a whole month telling me he had the perfect birthday present and hyping it up my birthday comes around he gives me a pink novelty sash that said the birthday be in sequins and that was it he didn't even buy me dinner when we went out that night if you are new to the channel you can subscribe i publish new videos every day until then check another video bye for now

Channel: Updoot Everything

Views: 112,646

Rating: 4.8987899 out of 5

Keywords: oh wait, you cant be serious, you cant be serious meme, are you serious, most awkward, #updootst, updoot, reddit, r/askreddit, askreddit, ask reddit, r/, \r, r\, best of reddit, reddit stories, reddit story, top posts, funniest posts, funny, funny posts, funny reddit stories, funny askreddit, reddit funny, askreddit funny, askreddit stories, reddit stories 2019, people of reddit, sub, reddit cringe, memes, toadfilms, updoot everything, updoot reddit, story, stories, rslash, comedy, fresh

Id: GX_aFPgOtgU

Length: 23min 58sec (1438 seconds)

Published: Sat Jul 18 2020