My skirt got caught on the concrete bench at work and got pulled down when I went to get up. I showed a crowd of co-workers my a*s. Everyone just kinda stood there trying not to laugh while I tried to collect my dignity. Bad day not to wear underwear.

I did community service with a youth group when I was around 10-11. Around the Christmas holiday, we bought and wrapped a bunch of gifts to take to an old folks home. I pick up a gift and walk over to this elderly gentleman. I’m swelling with pride and eager to drink in the large glass of “thank yous” I’m about to be served. He opens a really nice pair of slippers and looks at them for a moment: “What the hell am I supposed to do with these?” “You put them on your feet,” I delightfully exclaim. “I haven’t had feet since Vietnam.”

Maybe not *the* most awkward moment but it is up there. I was going on a date with a girl from tinder but she didn’t really show her face much in the photos but I thought, hey she’s pretty cool I’ll meet up with her and see what she’s like. The only thing I could see from the photos is that she’s Chinese (she also told me this later). So I got to the bar early and sat around and she texted that she was almost there. Then, as I was on my phone, Asian girl walks up and says ‘hey!’ So I kiss her on the cheek and hug her and go ‘hey! How are you?’ And tell her it’s nice to see her. Then she pauses, looks at me confused and says ‘can I get you a drink or anything from the menu?’ .... Turns out I kissed and hugged the waitress thinking it was my date and I just froze. ‘I’m so sorry oh my god are you not my date?’ And she goes ‘uh no...’ and we proceed to start laughing. I ask her to get me a double shot on gin while I get all red-faced. She was actually a really good sport about it. Later my date showed up, I told her what happened and we laughed it off. Won’t be going back to that bar.

Okay I already posted in this thread but I remembered something even worse. When I was in 2nd grade, my brother and I would always be picked up after school by my dad. We had a green van with a red stripe on the side. So my brother grabs my hand and storms us up to the car. He rips open the door, sits us down, buckles me in, and then says "Can we get mcdonalds on the way home?" We both look up and there is two middle aged adults sitting in the front seat that are OBVIOUSLY not our family. They stare at us, we stare at them. In my little brain we've been staring at eachother for at least ten minutes at this point. My brother unbuckles me, unbuckles himself, we get out and walk away. No words were exchanged. We then checked who was in the car before getting in from that point forward.

‘So are you two dating?’ He said yes at the same time I said no, to which his friend told him ‘I told you you didnt ask clearly enough’.

Was unexpectedly in the car ride with my boyfriend's parents on their way to sign their divorce papers.

Copied from another question I answered cos I'm too lazy to retype. I worked on a deli counter and that meant having to give customers free samples when they wanted to try a product. Let me first say I can be very socially awkward sometimes and I am not a very confident person - I was about 22 years old at the time. Female btw. Guy in his late 40s/early 50s comes to the counter and wants to try some olives - I go to the cupboard behind the counter and get a small plastic shot glass and a cocktail stick and put some olives in and go to offer the guy the glass. He holds up both arms and shows his hands are full with bags - he then proceeds to open his mouth up, indicating he wanted me to feed him the olive. I was kind of shocked and didn't really know what to do, I wanted to avoid conflict with the customer and have him go away so I just used a cocktail stick to get an olive and held it out towards him - he then ate the olive off the stick but let his mouth close round my fingers - it was honestly one of the most disgusting things that has ever happened to me and for ages after I could still feel the wetness of his mouth on my fingers - I must have scrubbed my hands a million times

Back when i was in college I got friendly with a girl in my sociology class. She brought a picture of her boyfriend in once to show me what he looked like (this was before Facebook was massively popular) I asked her who the guy next to him in the photo was, she replied ‘that’s me”. Mortified.

I've told this story once before, but when I was around 10 years old I was sleeping over at my best friend Juan's house. We usually stayed up really late playing and would sleep in until like 11 or 12, which I loved because I rarely got to do that at my house. At about 8 am his dad comes into the room and tells me to get dressed because he needed my help. His dad was a big drinker, so either his breath reeked of beer from last night or he had one for breakfast, either way he was a bit buzzed. He tells me he needs my help picking out a toy for Juan as a surprise and we were going to drive to Walmart. So we get in the car and drive down to the Wal-Mart which was like 10 minutes away from his house. It was a pretty awkward ride and he starts asking me questions to make small talk, like how I was like school and if I had a girlfriend yet. We get to the Walmart and he takes me to the you section and asks me what toy I think Juan would like. I walk around and see Darth Vader's Tie Fighter. Juan and I were huge Star Wars fans and even went to go see Empire Strikes Back in theaters when it was re-released, so I knew he would like it. He buys the toy and then we have another awkward car ride back. He thanks me for helping and asks me to keep it a secret. I changed into my pajamas again and tried to go back to sleep, but about 10 minutes later his dad comes in and surprises him with the toy and gives me a wink. I found out a few years later that the reason he had me go on this mission to get the toy was because he had been really drunk a couple of nights ago and hit Juan and he wanted to make it up to him. As far as I know that was the only time that ever happened, but I don't really know since we lost touch after 8th grade. It was just a such a strange and awkward morning.

I was sitting in class and the kid next to me farted and I said "God Bless you" as if it were a sneeze

One time in college, i snuck into my RA's room and hid under the blanket on his top bunk. My goal was to scare him when he came in and settled down a bit. He ended up coming in with his girlfriend and began making out with her. After a good (lifetime) couple moments, I jumped up and ran out. No saving it.

This poor girl walked into my lecture by mistake about halfway through. This particular professor really enjoys talking to all of his students and was super engaging even with 400+ students in his class. When the girl walked in, my professor stopped teaching, looked at the girl and asked if she was in the class. She said she was and began walking towards the front where the open seats were. This is a fairly large lecture hall and all 200 students (approx how many actually show up to class) were now forced to watch this poor girl walk towards a seat because the professor didn’t continue talking and just stared at her. She got close to the front and I think the pressure of the whole room got to her and she said, “actually no I’m not,” and turned around and we all had to watch this poor girl climb back up the stairs and out of the hall. I was literally watching my worst nightmare.

My 79 year old mother in law with Alzheimer’s telling us that she had had sex the previous night with another resident of her nursing home. (She had been celibate for 20 years up until then. We think.)

My ex wife later came out as a lesbian, and we divorced. Years later, I went to her wedding, where she married her now wife, which was one of my ex girlfriends.

When i was a kid, we were on holiday and decided to go to a church. While we were there i decided that i would be funny if i would slap my dad's a*s with both hands. So i ran in full speed to maximize the impact of the slap. I ended up slapping a stranger who also happened to walk next to a woman with a stroller in his hands which made me think it was my dad. It was even worse that my parents saw it as well. Edit: because people are asking what happened afterwards. My parents just laughed at me, which made the guy laugh as well and then we just left the church i think.

I used to run a restaurant and had inherited an employee with a sleigh of mental health issues. She had massive anxiety issues and just couldn't handle the pressure of working in a restaurant. She'd break down and cry over simple mistakes if she felt she was making too many. It was extremely unfortunate, but I was terribly under-prepared to coach someone like that. One day, during down-time, the cooks were shooting the s**t and recounting stories of weird ex co-workers. I opened up my yap and said: "who was the one who kept crying every time they'd screw up?" She was 2 ft away and literally responded with "Me.."

i was in the car with my girlfriends best friends moms and her other daughter, we made talk in the car and i just ended up asking what their favorite color was. they then told me the other daughter was actually blind... i had barely known these people and was in the car for another 20 mins, most awkward 20 of my life

I was at a funeral for one of my husband's relatives. On my way in, an employee of the funeral home asked me when I was due. I wasn't pregnant, but I am fat and was wearing an empire waist coat so I wasn't offended. As I signed the guestbook I corrected her and tried to defuse the situation with a joke about burning that coat later. But she just. wouldn't. stop. She kept trying to apologize and explain herself and I just wanted to run away. Then I was stuck in a small room with her for the next 2 hours.

I was at my aunts house for Christmas meetup (my whole family from my mother's side is always there) and we were just talking about some stuff, the "s****y life pro tips" subreddit came into my mind, and I told her that there are some tips like "you should drive faster when you are drunk, because driving drunk is dangerous and you get home faster". I was laughing, she just sat there, looking at me like frozen, and then told me with her voice breaking: "That would be funny, but did you know that one of my best friends died 2 months ago because he was driving drunk? And he was too fast." She then started to cry. I really wanted to stop existing at that moment, trust me

When I went on my first solo date back in high school. I had a huge crush on this girl, thought she was really cool and I loved her art and I couldn't believe she said said yes. We went to the zoo because it was free and we were just broke teenager and we had a blast. Went to grab some food at this place before having to split off to go home. Our trains were heading in the opposite directions and the entrances were across the street from each other, so I walked with her to her side to say goodbye. I closed my eyes and awkwardly leaned in to give her a kiss goodbye, and she went in more for a hug. I ended up headbutting her in the face and her nose started bleeding. I was so embarassed and didn't know what to say, so I just asked, "Are you okay?" She replied, "I think so." Still not knowing what to do I just said, "Okay, bye!" and then ran across the street to catch my train. It was so painfully awkward and embarrassing, I avoided her for weeks after that.

When I was a kid I hugged a random dude because I thought it was my dad. Even better how this dudes son was standing next to him.

I dunno if this is really the most awkward, but it was def awkward. I visited my bio dad's old church in Mississippi a few years ago and spoke to his old preacher for a moment. One important detail for this story is that my dad died when I was seven, so a pretty good while back. My grandma told the preacher who I was: "This is Pomelo Sr.'s daughter, Pomelo!" Preacher: "Ohh! Pomelo Sr! Tell him I said hi for me!" Me: "Sure thing!" My grandma's face was priceless. We agreed the preacher would feel really awkward when he remembered later that my dad was dead.

I am someone who never feels awkward and doesn't get embarressed, but this moment got me good. I was doing orientation for my college. I wanted to meet the dean of my department and make a good impression. I walk in his office and he is bent over behind his desk looking for something. I introduce myself and stick my hand out to shake his hand. He sits up and he has no arms. I look at him and look at my hand and I am freaking out. It felt like my hand was out there for an eternity and I did the only thing I could think of to do. I ran my hand through my hair and tried to play it off. He never said anything and just started talking to me but I felt like I was actually going to die of embarrassment.

When I was in elementary school, I hated using the public bathroom, and would always use the nurses bathroom instead. She was nice and understood this. However, one day I needed the bathroom and she was not around, so I let myself in. Shortly afterward, the nurse came back with a student and begun feeding him with a stomach tube. I was horrified. I realized that this was a closely guarded secret and decided to wait in the bathroom for it to end, hoping to sneak out later. But very shortly after it ended, more and more students with secret medical needs kept coming, and the hole kept getting deeper and deeper. Finally, after an hour and a half in the bathroom, I walked out. The nurse gave me a horrific glare, and the student looked just as uncomfortable as I felt. When I got back to class the teacher yelled at me in front of everyone for being gone so long, and I panicked/lied by yelling at the top of my lungs "I HAD DIARRHEA!". All the kids in class laughed at me, and the part that sucked was that I now knew most of their embarrassing secrets.

When I was 13 or 14 the guy I had a crush on took me to a park to talk and learn to know each other. We sat under some trees and everything was going pretty well, until guess a bird *sh*t* on my head while I was talking to him. I had to go back home to wash my hair a few times.

I was at a wedding and ran into my ex gf (dated for a couple years) and her husband. I am on good terms with both of them. The guy is a super nice dude, and my ex is an amazing person. And everyone was a little drunk and her husband kept saying weird s**t to me like: "Hey man, thanks for giving me a chance with your girl" "Im glad that you gave her to me" "Me and her wouldnt have been possible without you" and he just kept going on and on. Which btw, I had nothing to do with the two of them being together. She and I dated for a while, broke up, and moved on. So, this whole thing was all at complete random. And the whole time im looking at the girl and she is looking at me like.. okay dude please shut the f**k up now lol

I was hitchhiking across the US. which is awkward enough. some guy picked me up and half way through about a 20 minute drive down the road he decided to start talking about religion. okay cool, happens enough, most people try to convert you and such while hitching... this guy took another route by telling me about how everyone thinks Islam is a religion of violence and what have you... no, he wanted me to know it was a religion of peace... by yelling it to me at the top of his lungs for 10 minutes.

This was several years ago. I was over at my boyfriend’s parent’s house for his dad’s birthday. I’m fairly awkward and my boyfriend likes to joke, so he walks up to his dad and tells him I have a present for him. His dad turns to me and says “Well great! Let’s see it!” I did not have a present for him. I still cringe thinking about having to tell him I didn’t actually have a gift for him.

My family's not super religious but, when I was about 13, they decided to go to synagogue on Purim for some reason. Part of Purim involves reading from the Book of Esther, which has a part about Esther coming to see the king while he's sitting on his throne in the throne room and when he sees her, he stands up and extends the golden sceptre. When the rabbi got to that part, my 13 year old brain pictured Esther coming to see the king while he's sitting on the shi**er and burst out laughing. No one else laughed. Instead, everyone turned to stare at me and I had to explain myself to an entire room of people. We now celebrate Purim in the comfort of my parents' home.

Okay so me and some friends were at a restaurant and a buddy of mine was telling us about this new girl he just started going out with a few days back. Well another friend what started telling us about this girl that he banged the previous night. The conversation went on for a minute and finally somebody asked for the name of the girl that he had banged and it turns out it was a girl that the other friend had started dating a few days earlier. Cue narrowly avoided fight as we convinced him it's better to find out she's s****y now rather than later. The two guys still no longer speak though.

I was in some business college class and the professor was talking about something related to how celebrities brand themselves. Someone in the class brought up Shaun white as someone who had great celebrity branding but isn't really talked about a lot. The professor was Indian and said he wasn't familiar with who that was. So my genius a*s thought it would be perfect to say out loud "I'm talking about mountain dews baby." As a joke reference to that News cast where Shaun white said he had been drinking all night but was underage and the news person asked him what he meant so he responded with "I'm talking about mountain dews baby." And we'll no one seemed to knew about that or at least didn't think it was funny as silence rang through the classroom and professor awkwardly moved on to a new topic. Truly the most awkward situation I've been in and also the worst haunting moment of my life.

Got over charged a dollar at the store but did not want to have a conversation with the cashier