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30 Of The Most Uncomfortable Situations People Ever Found Themselves In, As Shared In This Thread
No matter how hard we try, some awkward situations are bound to happen. Whether it’s mixing up some unknown person with your mom, getting into the wrong car, or finding yourself in a delicate position where you shouldn’t be, all these situations happen to each and every one of us. Despite the fact that very often, they find a way to come back into our minds and make us cringe, these situations usually are also very funny to remember after a while. Having this in mind, Reddit user @u/YeastyMug asked others online “What's the most awkward situation you've ever been in?” The question that received almost 24k upvotes encouraged Reddit users to share awkward and sometimes hilarious situations that they found themselves in.
From unintentional mix-ups to pranks gone wrong, people online remembered various instances that made them feel embarrassed. How would you feel if you decided to strike up a conversation with a person and asked them “what’s their favorite color” and then learned that they’re blind, or had to witness two people finding out that they’re dating the same person? Don’t forget to leave your thoughts and stories of the most awkward situation that ever happened to you in the comments down below!
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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.
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.”
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
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.
I had a similar situation with my daughter's teammate. She unloaded her gear and I just watched until she realized. We just laughed and she turned around and found her mom.
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 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.
‘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.
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.
Oh s**t. Reading the comments, I remember my by far worst moment. 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
how would the kid know, he was obviously at fault because he was drunk, someone should have told the kid
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 happend 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 happend afterwards. My parents just laughed at me, which made the guy laugh as well and then we just left the church i think.
I did something similar when I was 8 or 9! Mom took me & my sister to the local department store (like a KMart, but much smaller). We split up and browsed a little, and I found something I wanted. I ran to my Mom, who was bending over a table of clothes, and I was yelling "Mommy!!" as I paddled this woman's backside. She stood up and turned around and, you guessed it, was not my Mom! Oh, the shame ...
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 was in line behind a pregnant woman when the male cashier asked her when she was due. She disgustedly responded "I'm not pregnant" and walked off with her cart. I made a vow that day to never ask a "pregnant" woman when she was due. They can be laying on the store floor in front of me giving birth and I will ask "Ma'am, you seem to be in distress - can I assist in any way?"
I was sitting in class and the kid next to me farted and I said "God Bless you" as if it were a sneeze
Here's my awkward fart story. I think I must have been about 15. You know how we can be at that age. Overly confident, like to show off, up for a challenge now and then. Maybe doing a bit of sports here and there. I had been cycling to school for maybe 3 months. I'd also recently started going to the gym. I was pretty pleased with myself. So I wanted to show off. I told one of my classmates to punch me in my stomach, not too hard obviously. We counted down...I tensed up, they punched...I farted. Good times!
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.
This happens in my dreams a lot, except, of course, I have no pants.
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.
The worst thing you can do is ruin it by trying to make it better 🙄
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.
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.
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.)
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.
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 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.
A few years afterr my mother died my wife and I had our daughter. I bumped into a friend who knew my mother had been ill but who hadn't seen us for a while. She was Scottish and when she saw my daughter she said: " Och she's beautiful, your mum must be dead proud!" My reply was, "Well you are half right"
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.."
...
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.
For me, every day is a bad day to not wear underwear. Especially in a dress or skirt.
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.
I adore the person who threw away all of the more relevant images and went with a photo of two LEGO Rebel pilots holding hands.
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.
I once had a bad experience partying with some friends, and I ended up having to walk ten miles back to town (and it was summer and hot as balls). Two miles away from my destination, an older gent in a Cadillac picks me up, and then proceeds to tell me that God told him to turn around and get me. He says, "Tell me, son, have you considered Jesus Christ as your Lord and savior?" I replied, " I would've, if he had picked me up eight miles before you did."
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 have been s**t on by a bird twice, and once i was with my grandma and it was right on my shoulder and it kinda splattered on her
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
Sounds like he was drunk & trying unsuccessfully to say "no hard feelings" lol
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.
when i was abt 6 i went up and held some random womans hand... my own mother was standing on the opposite side and laughing...
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.
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.
Seems harsh if they didn't know about each other. Bullet dodged, sort of
I have a loooong list of embarrassing stuff that's happened to me, but this is probably the funniest. I was at work and my supervisor called me. Before moving on to the thing he wanted me to do he asked how I was doing and I mentioned that my birthday was that weekend. He said hey, why don't you come up to the front office for afternoon tea? I said sure and when I arrived there was a cake on the table and a big "HAPPY BIRTHDAY!" banner had been hung up. And guess how I responded? By asking whose birthday it was. I have never seen so many blank confused stares before in my life. Then, just to emphasise the sitcom ridiculousness of the moment, the HAPPY BIRTHDAY banner broke the embarrassing silence by suddenly falling off the wall.
Please don't hate me, but I laughed. Thanks for sharing. I love awkward stories that aren't mine.
Load More Replies... Here's another one. I had just started a new job. I was sitting down at one of the tables, I think there were 6 other people. One of my coworkers asked me my name, so I told him my name. He repeated what he heard. I kept hearing my name, but with 1 letter difference. So I said my name again. He said the same thing, but I still thought he wasn't saying it right. We went back and forth 3 more times. Turns out he had a lisp, and had been saying it correctly the whole time.
Reminds me of one of the classic Penny Pollard's Diary books where Penny (an Australian kid) meets a guy from Texas who introduces himself as "Barb". She thinks it's a weird name but okay. Then, right at the end of the story, Penny's friend informs her that the guy's name is BOB and he probably spent the last week thinking she was making fun of his Texas drawl.
Load More Replies...
Fríck... I didn't want to share this, but here it comes: when I was around 10, my uncle had a gf, who had a tiny Yorkie named Robin. He was really cute and all, and one day, they all came to my house to have dinner and just meet him well. Suddenly, he grabs my uncle's foot with his front paws and starts swinging his hips. Everybody got mad and all, but I thought it was hilarious because he looked like he was dancing. So, a couple of hours later, my mom asks me to go to bed, so I thought it would be hilarious to drop to the floor, grab my mom's foot, and swing my hips like Robin did. They all looked at me horrified, and I was confused as to why they weren't laughing at my goodbye act. My mom later explained to me that Robin was... pleasuring himself with my uncle's foot, and I basically pretended to do the same. TLDR: I pretended to húmp my mom's foot without knowing what that meant
I have a loooong list of embarrassing stuff that's happened to me, but this is probably the funniest. I was at work and my supervisor called me. Before moving on to the thing he wanted me to do he asked how I was doing and I mentioned that my birthday was that weekend. He said hey, why don't you come up to the front office for afternoon tea? I said sure and when I arrived there was a cake on the table and a big "HAPPY BIRTHDAY!" banner had been hung up. And guess how I responded? By asking whose birthday it was. I have never seen so many blank confused stares before in my life. Then, just to emphasise the sitcom ridiculousness of the moment, the HAPPY BIRTHDAY banner broke the embarrassing silence by suddenly falling off the wall.
Please don't hate me, but I laughed. Thanks for sharing. I love awkward stories that aren't mine.
Load More Replies... Here's another one. I had just started a new job. I was sitting down at one of the tables, I think there were 6 other people. One of my coworkers asked me my name, so I told him my name. He repeated what he heard. I kept hearing my name, but with 1 letter difference. So I said my name again. He said the same thing, but I still thought he wasn't saying it right. We went back and forth 3 more times. Turns out he had a lisp, and had been saying it correctly the whole time.
Reminds me of one of the classic Penny Pollard's Diary books where Penny (an Australian kid) meets a guy from Texas who introduces himself as "Barb". She thinks it's a weird name but okay. Then, right at the end of the story, Penny's friend informs her that the guy's name is BOB and he probably spent the last week thinking she was making fun of his Texas drawl.
Load More Replies... Fríck... I didn't want to share this, but here it comes: when I was around 10, my uncle had a gf, who had a tiny Yorkie named Robin. He was really cute and all, and one day, they all came to my house to have dinner and just meet him well. Suddenly, he grabs my uncle's foot with his front paws and starts swinging his hips. Everybody got mad and all, but I thought it was hilarious because he looked like he was dancing. So, a couple of hours later, my mom asks me to go to bed, so I thought it would be hilarious to drop to the floor, grab my mom's foot, and swing my hips like Robin did. They all looked at me horrified, and I was confused as to why they weren't laughing at my goodbye act. My mom later explained to me that Robin was... pleasuring himself with my uncle's foot, and I basically pretended to do the same. TLDR: I pretended to húmp my mom's foot without knowing what that meant
