30 People Share The Most Awkward Situations They’ve Survived

Published 2 weeks ago

We’ve all been in uncomfortable situations that make us wish we could disappear on the spot. When a Reddit user posed the question, “What’s the most uncomfortable situation you’ve ever had to sit through?” it struck a chord with many, prompting a flood of responses detailing the most cringe-worthy and awkward moments netizens have endured.

Here are some of the worst experiences shared on the thread, offering both sympathy and a bit of schadenfreude.

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#1

Image source: sufishams, Pavel Danilyuk / pexels

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’.

#2

Image source: flannelfrankenstein, Vlada Karpovich / pexels

A new boss was hired for my department at work, and a high level woman from corporate was brought in to show him the ropes.

My new boss was a sleazy little weirdo. He sort of looked like Beans from “Even Stevens” crossed with Mads Mikkelsen. He kept awkwardly trying to flirt with this incredibly professional and visibly uninterested woman who was just trying to do her job by teaching him how to do his.

Things reached peak weirdness on her last day.

There we stood, my new boss on one side of the room, our guest on the other side, me in the middle doing some work.

New Boss: Well, are you ready to go to lunch? Corporate Woman: Yes, just let me run to the restroom first.

New Boss: Oh, why, you gotta POO-POO?

I have never in my entire life wished that I could turn into a puddle of liquid and slide out of that room, Secret World of Alex Mack style, than I did at that moment.

Fun Fact: He was fired a few months later, but that’s another story for another day.

#3

Image source: Moon_Jewel90

We had a farewell party for a colleague who was leaving our workplace and during her goodbye speech in front of everyone including our bosses, she started talking about how stressful the job was, didn’t get much support, wasn’t able to take proper breaks and that no job is worth the mental stress.
Needless to say, the room fell in awkward silence and our boss’s face looked uncomfortable.

#4

Image source: The_Intel_Guy, Mikhail Nilov / pexels

At my nans house I used to sleep in her bedroom on a sofa bed, there was a curtain separating my section of room from hers. When I was 14 and staying there for some time, I came upstairs to bed one evening after playing xbox, and got into bed. I then hear the unmistakable sounds of them boning and dirty talking eachother. They hadn’t heard me come up so I had the awful decision to make, either sit through this absolute pain for however long it lasted, or try and sneak across the incredibly creaky floorboards back downstairs without letting them know I overheard them.

Somehow (God was with me that day) I managed to sneak back downstairs, played some more xbox for a couple hours while contemplating my mental scarring, then went back to bed.

#5

Image source: Snake101333, Kindel Media / pexels

Every instance of my friends getting yelled at by their parents while I’m just standing there watching awkwardly.

Or vise versa.

#6

Image source: proxproxy, Matheus Bertelli / pexels

Alright everyone buckle up. Years ago my editor assigned me to do a story: an old civilian air command guy had died and his kids were going to spread his ashes from a plane over the lake where he helped find a downed aircraft decades ago. Nice local human interest piece. Two kids: son and daughter, both adults. The whole flight aspect was organized by a local, well-meaning family friend, let’s call him Jeff.

I drive to the tiny regional airport, walk to the tarmac and the son is there already. We shoot the s**t with the pilot and the son and Jeff when the daughter arrives. She’s extremely obese. The pilot and I realize we have a major problem. The pilot and Jeff and the son talk, then the son goes over to talk to his sister.

The wailing that came out of this woman, when told she couldn’t scatter her dad’s ashes because she was too fat, is burned into my brain. It was biblical. This woman was shrieking and sobbing and we could do nothing but watch as she collapsed on the runway and had a complete meltdown. I blame Jeff for not thinking ahead.

#7

Image source: Cute-as-Duck21, RDNE Stock project / pexels

A few years ago I went on a weekend girls trip with a friend. Her marriage was rocky and she needed to get away. Her husband dropped us off at the airport and picked us up after the trip, and we chatted casually in the car on the way back to their house. Everything seemed normal. Unbeknownst to me, he had specifically told her that if she went on this trip, he would leave her. Midway through the drive he told her he had a group of people at their house for her “intervention,” and that her car was already packed with her belongings and to get out. (I don’t think he knows what an intervention is, but whatevs.) So now I’m stuck in the backseat watching their marriage dissolve. We get to their house and people are standing on the front porch observing. The couple starts arguing in the driveway and I just wanted to leave so badly, but I needed my suitcase from the trunk. I had to interrupt them to ask him to open the trunk. And then my car was blocked in by the vehicles from the “intervention team,” so I had to interrupt again to ask how I could get out. It was so, so awkward.

#8

Image source: weezeloner, Ron Lach / pexels

Was at work and we were in a conference room about to have a meeting. Not sure what the meeting was about but my coworker “JT” thought he
It was a good idea to go around and ask us if we have ever cheated on our spouse. (He seemed to enjoy being on the cusp of being sent to HR)

I wasn’t married at the time so I said no. Every one says no. “BH” says yes. Now BH is a 60 something woman who’s as wholesome as Mr. Roger’s. Her voice is so soft. She was my first trainer when I started. She would talk and I’d get lulled to sleep..I had to drink 3 cups of coffee to avoid passing out. I hate coffee.

So when she says yes every one turns and looks.. JT is excited he’s like, “Ooohh, how many times? With who?” She says, “All the time, in my mind of course.”

He asks this lady who had worked at our agency in the past and left. She had just come back. JT asks her if she’s ever cheated.

She says no. “But my boyfriend constantly cheats on me. He doesn’t even try to hide it. He brings them to the house. But what am I going to do? I can’t afford to live on my own so I just sit there.”

JT is speechless. The rest of is don’t know what to do or say. It feels like we’re just sitting there for so long. Finally JT starts the meeting and we just start talking about our audits. It was so uncomfortable and sad.

#9

Image source: 87CSD, Jeremy Wong / pexels

My cousin’s wedding… His brother doing the best man speech.

He started it off with “You know what they say when a brother is the best man… No friends” and it spiraled downhill from there. It was so bad even their mother was trashing the best-man brother’s performance to me best time I saw her.

#10

Image source: The1joriss, Werner Pfennig / pexels

We had a business meeting with a big client. We’ve done work with them before and now we had to present our progress and if good, we’d be in big business. I presented first and all was good and nice. Next was my colleague. He had nothing. Like “dog ate my homework nothing”. What followed was an hour long rant from our big client at my boss and the colleague who screw up on how much time and money was wasted on this investment, how insulting this was, that they gonna cut their loses, never do business with us again and potentially sue us. Only for them to turn to me and say “no hard feelings, we liked your presentation”. Afterwards we three sat in the car back to the office in complete silence.

#11

Image source: RatLamington, Mizuno K / pexels

Maybe not the ‘most’, but I once had to sit through an hour of my incredibly sleazy and abusive ex-boss crying in front of all of us staff, and contain my urge to laugh.
Apparently he was feeling super ‘depressed’ and ‘stressed’ from how hard his life was. All the while embezzling money from us, forcing us to work without supplies or even electricity/internet, and blaming us for lack of productivity or income.
For an hour I strained to hold it all in while he sobbed like a hypocritical little b*tch in front of us. I later found out afterwards that everyone else was doing the same.
Most staff quit the workplace after this and the whole business went under from the boss’s shady money antics.

#12

Image source: Newfie-Girl1989, cottonbro studio / pexels

We were getting internet installed when I moved to the town I live in. I was 16 at the time. I had surgery the day before and was bleeding slightly off and on and kept a hand in my pants to prevent the material from sticking to my wound.

Anyway I thought the internet maintenance guy had left. I went to the living room and turned on the tv. It immediately was on some kids show. He walked back into the room and saw me with my hands in my pants.

In his view it could only possibly look like I was touching myself to kids shows. The silence was horrible as he slowly crept back out of the room.

#13

Image source: iroze, Andy Thrasher / flickr

Not me but a friend who worked in tech support. A client complains that, whenever the phone on her desk rings, weird character strings appear on her screen. He goes over there, she uses a basic landline and a word processor, no connection between the two.
Then, while he is there, her phone rings. She reaches over to it, leaning her huge bosom over the keyboard and of course, a string of characters begins to populate the word processor window.
He had to explain it to her.

#14

Image source: laevian, Tima Miroshnichenko / pexels

That would be the time in college that I got invited to a surprise birthday party for two of my other friends who shared a birthday. The party was very nicely planned with cake and presents for them, but I honestly shouldn’t have even gone… because, as some of the people at the party belatedly remembered, the party was being held on the day of _my_ birthday. I ended up third-wheeling a birthday party on my birthday. All the while some of my friends tried to forcibly include me in the festivities even though it had obviously not been part of the original plan.

I was able to at least leave early, but my friendship with that group was never really the same afterwards.

#15

Image source: Admirable-Rough-782, Polina Zimmerman / pexels

I was looking at my moms phone cause she wanted to show me some pictures from what she did that weekend. I swiped one too many times and came across one of her nudes. I felt my soul jolt out of my body seeing that s**t

#16

Image source: Jumpy-Purple7593, Daniel Borges / pexels

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.

#17

Image source: Sea_Drink7287, Vladimir Konoplev / pexels

I was at a wedding and the best man went off the rails during his speech at the reception. It was your stereotypical drunken rambling but it was the guy’s second marriage so he was talking about his first wife and how he’s good at most things except relationships, etc. People were audibly groaning and booing the guy and telling him to sit down. It was a truly Michael Scott moment. So awkward.

#18

Image source: Human-Magic-Marker, Karolina Grabowska / pexels

I had to tell an acquaintance/friend that his 15 year old son was sending me highly inappropriate (and illegal) texts. I’m a 41 year old man.

#19

Image source: sufishams, Tima Miroshnichenko / pexels

In the cinema. I interlocked my fingers with the kid sitting beside me for a full minute.

Turns out, he wasn’t my kid.

#20

Image source: Mobile_Prune_3207, Anna Tarazevich / pexels

A couple of years ago my business partner wanted to get massages (something I really, really don’t like) and she found a special for two. However, it was clearly meant for like, romantic twos. It was at a “spa” that was really just a converted house and the “massage room” was like the size of my bathroom. Small.

There was no sort of privacy between the beds and I am hugely conservative in that regard, whereas she was quite happy to rip all her clothes off in the room (no underwear even).

It was insanely uncomfortable and as soon as the massage was over, I got dressed and went to the bathroom. They still had to do a facial but I just did it in my actual clothes, no thank you.

#21

Image source: SmurtGurl, Alena Darmel Alena Darmel / pexels

Helping my friend pack up her stuff when leaving her husband. While he sat on the couch and cried.

#22

Image source: dilapidatedfungus, Anna Shvets / pexels

I’m a dental hygienist.

I had a patient that was flirting with me pretty heavily and telling me how pretty my eyes were. I’m used to compliments and got good at brushing them off, so I managed that this time.

I kind of forgot about him he rebooked 4 months later for another cleaning.

This time, he was more forward, saying how I’m young and beautiful.. and then he straight up asked me for an affair WHILE HIS WIFE AND KIDS WERE IN THE FRONT LOBBY WAITING.

I politely declined and finished my work, informed the Dr’s about it, and he was promptly banned from our office.

#23

Image source: Capelily, Janet McKnight / pexels

When I was about 16-17, I used to get really bad rashes under my breasts. It was painful, itchy, and gross. So I went to a dermatologist to help determine what was going on.

I’ve always had big boobs. But I was kinda introverted, shy and *very* self-conscious about my body. So, I was in the examination room, naked from the waist up, waiting for the doctor.

In walks the doctor, followed by about six interns or medical students. Nobody had asked me if it was okay to have a crowd staring at my breasts! While I sat and squirmed uncomfortably, the students all “thoughtfully” looked at my breasts. It was pure hell.

This was in the 70s.

I started using cotton-only bras and–surprise!–the rashes cleared up.

#24

Image source: chernygal, cottonbro studio / pexels

It was my senior year of high school. I was sitting in the library during a study hour with two girls in my class, I’ll call them Amy and Jane. Jane and I were actually fairly close, Amy didn’t really interact with us much outside of class but we got on with her well enough and neither of us had any other friends during study hour.

Jane had told me, just the day before, that she was pregnant. She was feeling a lot of mixed emotions about the whole thing. My high school had a very high teen pregnancy rate (there was a daycare in my school) and somehow the topic of another pregnant girl in my school came up.

Amy went on and on about how stupid it was to get pregnant in high school, how teen mothers aren’t good mothers, and that they’re just throwing their life away. Jane and I were both sat there, knowing she was pregnant. Finally, when Amy was done with her rant, Jane just looked at her, said “Amy, I’m pregnant.” She got up from the table and walked out of the library. Then I had to sit there with Amy for the rest of the hour and it was one of the most awkward hours of my life.

#25

Image source: Lemp_Triscuit11, Mohan Nannapaneni / pexels

Having my friends mom drive me back to my parents’ after we totaled said friend’s car ripping it around through a corn field. She couldn’t even like form full sentences, she just kept repeating different iterations of “… what were you *thinking?!*”

#26

Image source: Wise_Neighborhood499, Timur Weber / pexels

A joint therapy session with me & my therapist and my ex & his therapist. We all just sat there after I’d made a few points and waited for my ex to talk. After a while, it was so unbearable that I said “I don’t think this is working”.

Turns out my ex (and the therapists) thought I was talking about my marriage. Which…was also correct, but I was talking about the joint therapy. So I kind of accidentally ended my marriage that day, even though it wasn’t finalized for another year or so. I’m still embarrassed about it.

#27

Image source: thatoneguy2252, Pixabay / pexels

2 situations.

1st I did to myself. Long story short I didn’t get my suit fitted in time for my brother’s wedding and it was WAY too big. I looked like a fool and have never been more embarrassed. Him and his wife give me deserved s**t (all jokes, no bad intentions) but good lord I will never forgive that

2nd was recently when I went to see my cancer doctor for routine appt and while I was waiting a nurse came in to do quick vitals. She walked in and I politely asked her how her morning was and her answer was “my adult nephew was found unconscious last night and now might not live through the day”. Almost broke my neck with that verbal whiplash.

#28

Image source: IHadAnOpinion, RDNE Stock project / pexels

An autistic boy with a fixation on the Vietnam War sat next to a Vietnam veteran. I realize the boy couldn’t help it, but his mother sure as f**k could’ve.

#29

Image source: Silent-Zebra, Ron Lach / pexels

Family dinner with my brother and his high school girlfriend about twenty minutes after I had accidentally walked in on them. My brother kept sending me glances that said “please don’t tell mum and dad.” I kept that secret until I was an adult, I mentioned it to mum randomly one day and she just goes “oh, you poor thing! That must have been so traumatic! I had no idea!”

#30

Image source: drrmimi, RDNE Stock project / pexels

At church, 4th of July, and our pianist who thought she could sing (she couldn’t) singing Lee Greenwood’s I’m proud to be an American in the most god-awful high-pitched voice for the entire song. (She was using head voice the entire time for those in the know.) My husband and I were literally sitting there in shock, heads bowed, totally embarrassed with second hand embarrassment for her. This was about 20 years ago and we still talk about it around the 4th of July to this day. Had to be the longest few minutes of our lives.

Saumya Ratan

Saumya is an explorer of all things beautiful, quirky, and heartwarming. With her knack for art, design, photography, fun trivia, and internet humor, she takes you on a journey through the lighter side of pop culture.

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