25 Cringe-Worthy Moments That Made Serious Situations Super Awkward

Life is full of moments where we stumble, whether it’s a simple misstep or a monumental error. On Reddit, someone posed the question: “Oops, I just really f*ed up” moment?*” Unsurprisingly, the responses ranged from hilariously innocent to deeply cringe-worthy.

#1

Image source: ResurgentClusterfuck

When I was a server, I once asked a woman when she was due

She wasn’t pregnant

That was the last time I’ll ever assume that.

#2

Image source: stupidsexyf1anders

I prepaid for gas and never pumped it. I just paid, walked out the door and got in my car and drove off.

#3

Image source: Bigfops, uan Pablo Serrano

I was a brand new, right out of college Computer Programmer (back before we had Software Developers). We worked on minicomputers at the time and I had a long process that I needed to run which tied up my terminal. I went into the storage closet and dragged out another terminal so that I could do stuff while the process ran (an old version of multi-taking. You kids have no idea how easy you have it nowadays).

Well, because the new kid had two terminals, none of the other programmers wanted to look less productive, so everyone else did that. Then a week or so later the president of the company came back to the programmer area so he could mess around with some new hardware that came in. He looked around and said “Looks like everybody has two terminals now!”

Being a smart-a*s, I quicky quipped “Well, we all have two hands!” Which was met with silence. Huh, usually my quips get at least a chuckle.

It was then that I remembered that the president of the company did not, in fact, have two hands. He had a birth defect and one did not develop properly.

#4

Image source: Lobothehobosexual, Kaboompics.com

Wouldn’t say it’s my “favorite” but it’s one that haunts me the most. When I was in college I went to a computer in the school library. They were on these big circular desks with computers all around.

It was morning so I was kind of tired, some people were on the computers working already. And me being kind of tired still, I sat there got on a computer and then I stretched my arms and then stretched my legs out, and unfortunately the power strip for the computers was near me on my side and my foot his the button on the power strip and turned off all the computers on that desk

I don’t remember what she looked like but I still remember the kind of look of quiet anger and frustration of this girl that was working on a paper, just suddenly lose all of her work. She just quietly got up and walked away.

I would’ve felt better if she just stood up and punched me in the face.

#5

Image source: ShiraCheshire, Peyman Shojaei

That moment when the knife slips, and you don’t feel anything yet, but you look down at your hand and realize what you’ve done…

#6

Image source: sasqualtch, Andrea Piacquadio

I got a text from one of my higher ups in the military about needing to change barracks rooms and he had a b****y tone, so I immediately screenshotted it and sent it to my GF with the caption “look at this b***h” but as soon as I hit “send” I saw I sent it back to him instead. The following days were not fun for me.

#7

Image source: OreoKing10, Getty Images

Got a basketball stuck high up in a tree one time, I thought it would be a good idea to throw a rock at it to dislodge it. My dad’s car was under the tree and the rock went right through the windshield on the way down.

#8

Image source: LoweeLL, cottonbro studio

Recommended a buddy of mine to work with me. Gave him extremely high praises because he truly does deserve it..

He failed the d**g test..

Last time I ever recommend anyone for a job.

#9

I used to work the receiving dock and knew all the truck drivers. One was Bob, 6’6″ and built like a NFL player.

I transferred to the second plant about 4 miles down the road, and it was mostly new hires who didn’t know me or that I use to work receiving. One day Bob shows up because his load needed to be dropped at the 2nd plant. It was just about lunch time so he said he would wait.

A bunch of us and Bob went to the bathroom to wash up for lunch. Bob sighed, and I said “Cheer up it could be worse.”

“It already is. My wife thinks she is pregnant.”

Without hesitation I replied, “So, is it yours?”

Everyone in the room had OO eyes and they were all thinking this guy has done f****d up and is about to be beaten to death.

Bob just looked at me and said, “Yeah, that was the first thing I asked her.”.

Image source: Empereor_Norton

#10

Image source: EarHumble1248, vwwally

It was my first day as a help desk technician. I had been asked to change printer toner on the main printer in the company office.

I pulled the black toner out, and I dropped it. The thing exploded like it was a new years’ fireworks show. All over me, all over the floor, all over the printer….even 10 years later, I still think they’re digging toner out of the cubicle.

I looked like one of those cartoon images where Elmer Fudd was given a bomb just before it exploded and then it blew up.

Fortunately my boss was my friend, and he laughed his a*s off. Photos, email distribution, the works.

I made my best effort to clean it up until the facilities guy shoved me aside and said “Let me do it.” with his nuclear powered backpack vacuum.

I’m just glad it wasn’t the yellow I dropped. I didn’t want to look like I peed my pants all day.

#11

Image source: CelestialDahlia, MART PRODUCTION

When I accidentally sent a spicy text meant for my partner to my family group chat. The sheer panic that set in as I realized what I’d done was unreal.

#12

Image source: PowerSkunk92, timbo637

Somehow when I was in high school (late 90s), everyone who still lived at home at the time had waterbeds, which made moving into a new house a bit of a pain in the a*s. I remember getting all of the beds set up and having the garden hose in the last one to fill it up. While this is happening, the van with the rest of the house in it arrived and everyone goes to start unloading.

No one is watching this last waterbed fill.

Several hours later over pizza, my sister comes into the kitchen and says that the carpet in the hallway is wet. And we all had a collective “Really f****d up” moment.

The bed had overfilled to the point that the fill nozzle was like three feet over the sides of the frame, the mattress was horribly stretched, the hose had detached and was just dumping onto the floor. It took several hours to shopvac the water out of the carpet, but we were able to deflate and salvage the mattress at least.

#13

Image source: GrapefruitFar1242, Tima Miroshnichenko

The joiner at my work place taking off the shield guard on the saw so he could drag the thing he was working on through… along with 3 knuckles and a chunk of the back of his hand.

Last I heard he had to have multiple amputations.

I was working nearby when it happened and all I could hear was “Oh god oh f**k oh no oh that’s bad oh f**k oh god” etc etc.

#14

So when I was in school, gay was a very popular word to describe things. Most people here will know what I mean when I say it was never said with the intent of ‘oh that is homosexual’ more of a ‘oh thats annoying’ thing (not that it makes the use of the word any better, but the intent when I say it is important here).

Me and one friend thought we were peak hilarious when we swapped out gay for lesbian when we’d speak like that, peak 13/14 year old humour.

Anyway one day I was in an argument with my older sister, we’d both used the word gay in the way I described growing up so in the heat of the moment I went to say ‘oh shut up, gay’ jokingly and instead said ‘oh shut up, lesbian’ With a bit more venom in the word than I anticipated.

My sister was in a relationship with another woman at the time, absolute instant regret and horror when I said it, shock on her face too, instantly ends the conversation. It’s one of those things that just creeps back into your head every couple months. I eventually brought it up a year or two back and she says she has no memory of it and its hilarious. That s**t stewed in my mind for years and she didn’t care, the bastard.

Image source: LKRTM1874

#15

A colleague at work wanted to try out some software that didn’t have a trial, so I downloaded a torrent version.

He installed it and about half hour later he came to me and said his computer was acting funny. I went and had a look and I could see each file one by one being encrypted by ransomware.

This was just the beginning.

His computer was hooked up to the company’s Google Drive, so all of his infected files were synced to the cloud. From there, it was then synced to every machine in the office. One by one, everyone’s files were being encrypted right in front of them.

At this point I started panicking and called my senior dev who rushed in from his day off.

Then, the ultimate happened. Our company’s files were all backed up on a local NAS drive, so of course, the infected files were synced to that, and just as before, one by one, the NAS files were being nuked.

In the space of an hour, I had single-handedly wiped out thousands of hours worth of client work.

Best part, because it was a new type of virus. There was no fix for it, no decryption utility.

The files were gone. We removed everyone’s hard drives and put them in “cold storage” and we pretty much started from scratch.

Lesson to be learned, never back up your redundancies on-site, never download illegal torrents on company computers.

Somehow, I was not fired, but I fully expected to be.

Image source: ConduciveMammal

#16

Image source: milkandcookies21, Andrea Piacquadio

I was fresh out of undergrad and working at a small university. One of my coworkers came out crying so I asked her what was wrong. She said she just got a phone call that her sister lost her leg. I didn’t mean to say it, but my brain decided for me, and I replied to her “Oh, well I hope she finds it!”…. Her sister’s leg was run over and cut off by a trolley. They did not need help locating it.

She did take the joke like a champ though and even thanked me later for “adding some light hearted humor, and making her laugh”. Like her sister’s leg, I left the part where I didn’t mean to say it cut off.

#17

Image source: fake-august, Scott Graham

I had just started a new job as a registered sales assistant at a major firm. All fresh and excited with my new Series 7 I was ready to do trades.

My supervisor handed me a client’s statement and told me to liquidate the holdings…not noticing some of the holdings were highlighted I proceeded to liquidate the entire account instead of about 25% of it. Worst part I didn’t realize it until she came over (she could see the trades in real time as I was selling) and asked me WHAT WAS I DOING?!

I got red, heated and ran to compliance to get it fixed. Our compliance officer told me to dry my tears, take a walk and have a coke – he called it my rite of passage. Never had another trading error.

#18

Image source: ice-eight, Erik Odiin

When I was in college and my dad lived in DC, he bought me a plane ticket to go visit him. I went to Texas A&M so the closest major city was Houston, and I’d never flown out of there before. So I arrive at the airport about an hour and a half before my flight, and I can’t find the check in for Southwest Airlines. So I asked an airport employee and he gave me this look like “dude please tell me you’re not being serious right now.” I was at IAH and Southwest only flies out of Hobby, which is all the way on the other side of Houston, and it was rush hour. I did not make the flight.

#19

Image source: WearyEnthusiasm6643, CookiesAreGodz-64

I just started a new cheffing job at my dream restaurant.

I had been there for a couple weeks, and prepping in the back kitchen, when I went to put a cutting board back on the rack.

I didn’t realize it was falling to the side, and it was too late when hundreds, if not thousands, of dollars of restaurant white dishware fell, shattering to the ground. plates, bowls, ramekins, trays, you name it.

still can’t believe they kept me.

#20

Image source: Tasty_Rip_4267, Ave Calvar

I thought it was a fart and s**t myself legit like two days ago.

#21

I came home to my parents house pretty drunk, they were asleep. I proceeded to slip on the stairs going down to my bedroom and in falling down ripped the entire 10 foot bannister off the wall.

Somehow, they did not wake up.

Told them the next day I just slipped and fell and it was an accidnet and they believed me. Helped my Dad put it back up the next day. Years later, I’m pretty sure he knew, but he’s never asked about it.

Image source: TriscuitCracker

#22

When I was around 8 years old I answered the phone to hear a family friend on the other end. She has a lot of kids and they’d make a ruckus during church (we were Mormons at the time) so I shouted to my mom, “Mom! The lady from church who cannot watch her kids is on the phone!!” My a*s got whooped and I had to say sorry to her that very next Sunday. But I still don’t feel bad about it cuz that’s how everyone described her behind her back??‍♂️.

Image source: Bednars_lovechild69

#23

Image source: Euphoric_External770, Mikhail Nilov

Intended to send my daughter, who was home alone, a pic of my credit card so she could doordash food. Sent it to the mom group chat of my son’s football team by mistake.

#24

Image source: WhyBeard, olia danilevich

A few years ago, I was working at an HMV online warehouse back when CDs and DVDs were still a thing. We had this persistent issue that had been dragging on for months. At one point, some big bosses came for a visit, including the CEO of the entire company. During the visit, one of the floor staff decided to ask the CEO about the issue in front of the entire workforce. He played along and said he’d “look into it,” which we all knew was unlikely since it was so far below his pay grade.

Fast forward a few weeks, and I was sending yet another email about the same issue. Half-jokingly, I added, “as [CEO’s name] said he would look into it”. The problem? I wasn’t 100% sure how to spell his name. So, I started typing it into the CC field to let it auto-populate, thinking I’d delete it after.

Except I didn’t.

I hit send.

So now the CEO had an email from some nobody 75 levels below him, looking like I was whining and holding him personally accountable for an issue he definitely didn’t need to deal with. I imagine he opened that email like, “Who the hell is this guy?”

Thankfully, my manager was an absolute legend. After laughing his head off at my expense, he smoothed things over by sending an apology email on my behalf.

I’m getting a hot neck just thinking about it.

#25

Image source: Impressive-Sea3367, Curated Lifestyle

I had just turned 18 and went to get my first tattoo. My mom hates tattoos, so I made sure to get it in a place she was unlikely to see, on my hip. Well, we both smoked cigarettes at the time, and she had run out. So when I got home, she rummaged through my purse to find some cigarettes, and she found the damn receipt for the tattoo. I hadn’t even been home for 15 minutes.