What Is the Hardest You Have Ever Failed With a Boy?

what is the hardest you have ever failed with a boy i was a year younger than everyone else in my class from a lower economic background so no major brand name clothes no giant cd collections no pocket money etc and not at all well liked the worst part was probably that the other kids could see how desperately i wanted to fit in which of course just made them meaner so i liked a fellow in my grade 5 class but i wouldn't have dreamed of doing anything about it then one day the top three girls in the class excitedly corrolled me into a corner during recess telling me that my crush wanted to speak with me nervous as all heck i waited and when he came he said the nicest things to me anyone had ever said just the kinds of things a girl with low self-confidence would kill to hear from someone anyone once in a while when he left i felt like i was walking on air i could hardly believe that anyone would think such nice things about me and i wanted to savor it then the top three girls returned with all the other girls in the class tagging along and asked endless questions about what had transpired suddenly i had information that made me popular too so i told them a big mistake as soon as i'd finished relaying what the fellow had said he leaped out from behind a corner along with all the other boys in the class surrounded by the entire class i was forced to listen as he laughed and took back everything he'd said throwing in a lot of vicious words in their stead how could you ever even think for a second that someone like you had a chance with someone like me was one phrase that still comes to mind but a lot of the personal remarks about my appearance my intelligence my laugh my teeth etc also bore their way deep inside suffice it to say i was devastated and as soon as the circle let me leave i tore out and away for a hill at the edge of our school where i proceeded to ball my eyes out the really sucky bit is that one of the students later informed our teacher that i had tried to commit suicide by leaping off that hill and the teacher took it to the principal and the principal called home and well my home life was really crappy already but it got shittier when my parents found out about the purported attempt i was so afraid of my mother who came tearing after me in the most aggressive way imaginable after my father told her what the school had said that i hid under my sister's bed in fear she hauled me out by my hair dragging me across the floor and locking us both in my room so we could talk about what had happened for years after both she and my father would bring up that perpetrated suicide attempts whenever they were upset over other matters at home like my depression was the icing on the cake of all their life's problems tl dr worst experience ever god damn that was rough to read in with this other poster you win i met a boy in my freshman year of high school and we became friends pretty quickly but it wasn't until sophomore year that i started realizing that i really liked him we had a ton in common and ended up going to two homecoming dances and junior prom together but we never officially went out or had any real dates or anything like that the most we ever did was play smash brothers and ddr in my basement i guess full stop so we get to senior a year and i still haven't really told him how i feel about him when another girl mutual friend asks me what are you going to do if he starts going out with someone else i replied with something like i'll get over it i guess since i'm not really the type to go after a guy who's taken and pretty much the next day she asked him out for a couple of months that felt like the most epic failure on the face of the planet don't worry everything went all right in the end he's gay xd happy ending d in elementary school i would chase this boy around in art class and try to kiss him he complained to the teacher and i got sent home for sexual harassment freshman year didn't want to dorm wanted to be cool and live off campus yeah rented a room from guy who'd inherited a huge house soon found out we had a lot in common sharing meals he was a great cook going to concerts gardening in his backyard etc he was an elementary school teacher and invited me to all the social events at his school so i fell desperately in love with him and spent many nights alone in my room wondering if that was the night he'd finally show up to ravage me about six months in we throw a huge birthday party for him everything was lovely good food good weed good company in the wee hours when everyone started drifting home one friend a fellow teacher of his stayed to help with the cleanup after everything had been put away i was giving the friend a big thank you goodbye hug when my roommate came up behind me and put his arms around the two of us it felt lovely to be sandwiched between two tall gorgeous men so i luxuriated in the warmth for a minute or two then i tilted my head to find that they were engaged in a deep throat plunging kiss td il i was the decoy girlfriend to a man who wasn't ready to come out i had an amazingly adorable japanese tutor in high school it never occurred to me that a hot boy would be into me so when he asked me if i had a date to prom i said that i wouldn't be going and asked him what word described being utterly uninterested in something i have no idea why i worded it so harshly either i didn't get that he had asked me out until someone told me much later i was the boy in the scenario but i'm counting this as a pretty solid female fail at a friend's house in hs we had a few people over and one of the chicks she didn't go to our school and i didn't know her and i were hitting it off we all went to the living room to watch a movie and she sat right next to me we started fooling around and out of nowhere her hand is in my pants and jerking me off i was in heaven for the sheer unexpected hj then someone answers the door and in walks her mother to pick her up i was kinda mortified and she must have been too but her response was to just keep yanking away while her mom stares directly at me she kept fapping away and i was going limper by the second and trying to escape she kept it up for 30 seconds or more which felt like an eternity finally her mom freaks out and starts yelling she starts yelling back all while still pumping away and now all of my friends and her mom are watching she eventually got up and they began arguing right there and she was explaining emphatically that she didn't want to give me blue balls as her mom is yelling for her to get in the car she looks at me crying and asks me to call her yeah i never did and i had that story circulating for years my senior year of high school i had a quiet crush on one of my friends that grew steadily larger as we approached graduation he asked me to the formal prom for the us unexpectedly i was thrilled but cynical i knew he'd probably asked me a friend just to escape the teenage dramas surrounding the whole thing that's what i would have done at the after party we all had a bit to drink and i made my big move i noticed him wandering off and put myself on a path that would intersect his the party was in a neighborhood of sparse houses with big yards and bushlands we wandered along the road talking and generally being friendly and flirty i knew him fairly well which only made me more nervous we sat down on the grass then made out i was high on success and confidence i touched a dong for the first time we said reasonably romantic things and spent the rest of the night with our hands in each other's back pockets i was pretty stoked we fell asleep on a porch spooning next afternoon i find out that he asked house another girl not four hours after our exploits they're engaged now ouch little did she know that she was touching a dong the whole night when i was 13 i was really awkward and kinda boyish looking i was badly teased and bullied at the last year of primary school so i was really desperate for people to like me in high school there was this boy in my computer class who hadn't gone to my primary school so didn't know he was supposed to not be nice to me anyway these popular kids became friends with him and told him i was a nerd and a lesbian and all that lovely stuff i didn't know he had decided to not like me anymore and so he came up to me in class and said hey lenny and i was all hey what's up can i ask you something i'm okay super embarrassed blushing did it hurt what did it hurt having your face smashed against that brick wall that made you so ugly and everyone heard it and laughed and laughed ugh high school [ __ ] sucked sometimes whoa kids can be super buttholes huh hug stayed up all night with him watching star trek and evangelion i tried to escalate things but he just wasn't responding i slept on the couch i hope he's not a redditor in high school me and this boy i fancied would hang out a lot one day our school had a half day and i was going to walk with him to his house after school to watch tv together except i didn't want to watch tv if you know what i mean we're standing in the hallway at school and one of his friends asks him what he was up to the rest of the day and he replied something along the lines of a star named alice is coming over but i have no idea why he acted like his day was ruined because i was coming over i felt like crap my theory is that broth when together tend to act as if they are not interested in girls as much as the girls are interested in them in essence they try to act like they don't need the girls because it's weak when i was younger and available i just assumed that anyone who expressed interest didn't yet know me well enough hadn't yet gotten a good enough look at me to realize how totally undesirable i was in retrospect i wasted some pretty cute years and the chance to maybe have been close to some pretty worthwhile guys but spared them some crazy good news i grew up got myself in better order and it doesn't have to end in forever alone tl dr i lacked even the confidence to try enough to fail oh yes this is when a quote from crap my dad says comes to mind after seeing a beautiful woman and telling his dad that she was too hot to be with a guy like him his dad responded let women figure out why they won't screw you don't do it for them my mom and i had been arguing in front of my little brother because i like asians and redheads but i guess she expected me to go out only with people from our all black except for us neighborhood because she said i would never find an asian or redhead to date the three of us went to the grocery store and my brother yells out there's an asian guy i looked up to see the hottest asian guy i have ever seen in person still and yes i still remember what he looks like he was that hot and i have seen many asian guys in person since walking towards me i stared at him dumbfounded by his hotness for a moment he had obviously heard my brother and i was i was too embarrassed to say anything when i was in college i had a block of three hours between classes on tuesdays and thursdays and it wasn't feasible for me to go home and come back so i'd hang out at a nearby mall there was a new japanese restaurant in the food court with a cute guy working there so i made small talk with him his uncle owned the place and knew i liked the guy but the guy seemed oblivious eventually i gave the guy my phone number so he called and asked what i wanted to talk about i don't remember what i said but his reply was oh i thought you wanted a special order or something then he asked how old i was i said 16 and he said i'm 21. you're like my little sister or something he also said he didn't want to date because he had to go back to japan soon he was just over here to help his uncle start the restaurant the next time i went back the uncle and the guy saw me coming into the food court and the uncle said in japanese i'd never told them i spoke it something to the effects of stop being an idiot she's cute and smart you can take her back to japan with you and the guy went into the back to avoid talking to me i was too embarrassed to go into the food court for a long time as a man i look through all these comments hoping to see a story about myself then i realized either way i would be disappointed i don't find a story and realize a girl didn't secretly like me i do find a story and realize that a girl secretly liked me you and me both buddy when i was 16 i was totally in love with this guy we hooked up a few times then he broke it off with me because we were too similar and would be better as friends he was right but man that hurt a few weeks later we met at a club and we got talking and i told him that even when i'm on a diet if i want a mars bar i just have it then i proceeded to mouth rape him we did end up being friends for the next 10 years but i sure hope he forgot that mars bar comment it still makes me die a little inside number no i don't understand any of this ladies piece of advice guys don't read between the lines i can't tell you how many times i've heard it's about freaking time didn't you get my earlier hints from a woman after she made the first move really most xyz are somewhat clueless when it comes to woman subtly and with the modern creep label are somewhat scared if you want a guy be obvious and yes we do appreciate a woman making the first move and no we don't for the most part there are always exceptions bad mouth women who are assertive guys don't read between the lines heck most times guys don't even read the lines often we're too oblivious to even open the freaking book i had a really big crush on a friend for ages eventually we ended up getting really drunk and sleeping together i thought finally it's happening the next day he said we should forget it happened because he didn't want to ruin our friendship fml and i thought that only boys can be friendzoned i don't know why but i'd like to high-five you [Music] kind of similar to what an oldimation i used to drive past my crush's house even though it was nowhere near mine on the off chance i'd see him i would try to think of any random thing that i could start up a conversation about i'd do the whole walking past thing try to figure out stuff he liked so i could seem similar etc for his birthday i had made a card about all of the great things about him it was supposed to be funny but i'm pretty sure it came off as weird of course he ended up dating my best friend and later told me he knew i had a crush on him the whole time to be fair i lived in a really small town so obsessive crushes were kind of the most entertaining thing around my first year of college i had been dating a guy that i'd previously been just friends with for a few days and he and some of my friends went out for my birthday we went back to my room and cuddled and watched a movie and later made out then i started grinding against his leg this was at about three or four a.m thinking he might want to go a little farther than making out but then he decided to go home because it was late after that day he got pneumonia and it was concurrently finals week so i'd walk like 30 minutes in the dark through scary allies and such to bring him ginger ale and crackers and to get him a thermometer and a bag of skittles then he broke up with me a friend later told me he thought i was too clingy then he went on to date a really pretty blonde sorority girl and i realized that we're better as friends means i don't ever want to talk to you again so i'd walk like 30 minutes in the dark through scary allies and such to bring him ginger ale and crackers and to get him a thermometer and a bag of skittles i had a girl who did pretty much the same thing for me i did the only plausible thing i married her we've been together for 10 years frick that guy he was a dong one time i kissed a boy on a school bus without warning and told him that he could get off at my stop and we could walk to my house because my parents weren't home he said no because he was going to miss dragon ball z girls if you want a guide to know you're interested just start massaging his crotch trust me he'll get the message and he won't cry rape if he's not entrusted i am a guy and i can confirm this little on jim zucherdork didn't realize that she could talk sports all she wanted to in high school but it generally wouldn't work around the boys in the sci-fi club because they didn't know what she was going on about oh god this is bad when i was in sixth grade i had a huge crush on this boy i'd been listening to 98 degrees song invisible man non-stop for about a month thinking of this guy clearly according to my sixth grade model of how the world worked if i started leaving him anonymous notes saying how much i was pining for him he would fall madly in love with the mysterious girl and yearned to know who she was and we would live happily ever after so i started leaving notes in his locker but when he didn't get them who actually looks in their locker i started changing my strategy i started slipping them into his bag with obvious references to that goddamn song and other statements that i thought would demonstrate the intensity of my affections but which really just demonstrated the pathetic desperation of my infatuation i signed them the invisible woman of course everyone knew how much i loved that song because i talked about it constantly and after he mentioned the note to one of the coolest and most beautiful girls in the class she immediately figured out who it was together they looked in his locker for more notes and found a a backlog and they read them together naturally she told everyone what a freak i was i was not exactly one of the cool kids and he was cooler than cool and i found out that i'd been discovered via merciless mockery however my hope was ironclad so i sucked it up and asked him out he said no and started going with the girl who exposed my embarrassment to the world who then mocked me for years to come epilogue i'm 25 now i ran into her a few years ago and let me just say revenge is a dish best served fat up vote for the epilogue that was tremendous in middle school i had a crush on this boy named steven i was in my math class that day and somehow my teacher had come to find out that i had a crush on stephen teacher proceeded to embarrass me teacher hey stephen i will give you an a if you go out with nancy that's my name stephen that crap was wrong i had a very very extensive crush on a guy in high school it started sophomore year and after enough friendliness and spending most of the day together we had all the same classes for over a year i finally decided one weekend to ask him out we had an uncharacteristically deep and personal conversation over i am on saturday night and it took all my effort to not ask him out right there but i managed to withhold because i wanted to be classy and ask him out in person sunday evening rolls around and i'm giddy with excitement about asking him out the next morning before heading to bed i decided to check my facebook out of habit and there it was in my news feed i saw that his relationship status had changed debating my worst enemy ex-best friend from elementary school whom i hadn't spoken to in years i pretty much died i was completely crushed and cried for days months passed and they remain together we remain friends and i pined over another year later senior year at this point they were still together and i decided that i needed to say something so i confessed my long-standing love for him as we drove around in the dark for three hours he confirmed that had i asked him out that saturday he would definitely had said yes i still can't help but love him college comes and we end up at the same college he's still with spiteful b i finally decide four years is too long to pine for someone and start pursuing a relationship with someone i met at college the day after my new boyfriend and i go official he breaks up with spiteful bee i've taken it as a sign from the universe that we should never be together tl dr i missed being able to date my four year long crush by 12 hours twice with over 1 500 comments in this thread at this point no one will read this but here it is anyway my best friend's brother from my teenage years with over 1 500 comments in this thread at this point no one will read this but here it is anyway some of us order things by newest really close guy friend who i've had a crush on for years tells me that when he kissed me and cuddled with me all night it was just because he was drunk i still feel awful just thinking about it totally been there there is really no phrase for how you feel after something like that probably going to be buried but what the heck at least mine are actual rejections one during high school this guy moved in with his aunt and uncle because his house had been destroyed by hurricane katrina he had the greatest accent ever and i fell pretty hard but he didn't get that i liked him so i made him a mix cd god i'm awkward and put it in his locker with a note saying i liked him our lockers didn't have locks on them well he showed it to all of his friends some of whom were my friends and some of whom weren't at all my friends i was mercilessly teased for the rest of the school year until he moved back to new orleans 2 freshman year of college i had a crush on this guy who was in a big group of friends with me we would talk all the time and when we got drunk we almost always did the drunk cuddle thing and by the end of the year i was like fricking he clearly hasn't got the message yet i'll just tell him so right before i was going to leave for the airport i told him i liked him and he said yeah i know i tried to explain to him that i liked him in the special way and he again said yeah i know so i just left for the bus ending up being like two hours early for my flight because i didn't know what else to do things were getting hot and heaving with a boy and i was going down on him i stopped to take a breather for a second and get into a more comfortable position when my elbow slipped his dong ran down the side of my face and i hadn't shaved in a few days it hurt him and kinda killed the mood coma things were getting hot and heaving with a boy and i was going down on him nice como i stopped to take a breather for a second and get into a more comfortable position when my elbow slipped go on comma his dong ran down the side of my face and i hadn't shaved in a few days oh guy fail stories being socially awkward and not being able to get the girl to like them a girl fail stories accidentally making people they like feel crap about themselves i sent somebody a valentine's day card in year eight when he got it he was so horrified that i told him it was a joke and he believed me failure level was pretty high i was secretly sleeping with a friend of mine and i was starting to like him too much it was complicated as we were hiding it from everyone else and one of my friends who used to sleep with him would have been p had she found out which he did but that's another story so after we snuck gramanasis sneaked you off together the last time and got the sex on i said immediately after we can't do this anymore the look on his face was stunned i said i'm starting to like you too much and if we keep doing this i'm going to want more and you don't date his reply maybe it's about time i started to date and i said well i'm not really ready my lack of total confidence resulted in me turning him down i assume he couldn't possibly want me to be his girlfriend woof now he's dating another friend of mine who is way hotter than me and a gamer forever alone if you are new to the channel you can subscribe i publish new videos every day until then check another video [Music] so bye for now

Channel: UE Studios

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Keywords: most embarrassing moments, most embarrassing, fails, fail moments, fail moments funny, #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 2021, people of reddit, sub, reddit cringe, memes, toadfilms, updoot everything, updoot reddit, story, stories, rslash, comedy, fresh

Id: FUGwkqQQSUY

Length: 25min 29sec (1529 seconds)

Published: Mon Apr 26 2021