December 28, 2022 | Violet Newbury

The Most Embarrassing "Oops!" Moments


Whether it’s saying something without thinking or falling flat by doing something stupid, everyone has had that one embarrassing moment they wished they could take back. These Redditors share incidents that left them thinking, “Oops, what did I just do?" Embarrassing doesn’t even begin to describe the outcome.


1. Hanging By A Thread

Long ago, I worked for a pest-control business as a favor to the owner, my father-in-law. I ended up at the house of one of the home builders that I used to do construction work for, and he had a serious pest problem. Ants had found their way into the house through the eaves, across the attic, and into the kitchen pantry, which was located in the middle of the house.

I quickly dispatched the ant hill outside. In an effort to impress both this builder and my father-in-law, I proceeded into the attic to deal with the miscreant ants who had found fit to blaze the trail in the first place. After spraying a considerable amount of pesticide in their attic, I was convinced of my ultimate success at ridding the home of said nuisance.

Upon backing out of the area in the attic, I took a fateful step off of the walkway and through the sheetrock ceiling. I found myself hanging precariously about 10 feet above the living room floor of the builder's home. He, his wife, and her 80-something-year-old mother just stared up at me in disbelief as I hung from the joists, looking down at them. All I could say was, "I took care of the ants".

The Most Embarrassing "Oops!" MomentsFreepik, master1305

2. Hidden Agenda

I was going to grab a brew on my way home from sporting. I walked up to the bar and saw an old friend sitting in front of it. I hadn’t seen him in years, so I walked up, grabbed a chair, and started a conversation. After I sat down and started talking, I noticed he responded awkwardly.

I looked sideward, and I noticed he was not alone but with my ex. She was hidden from view by a big plant. Apparently, he got the news of our very recent breakup and gave her a call to grab some drinks.

The Most Embarrassing "Oops!" MomentsPexels

3. A Matter Of Vise

In middle school woodworking class, the teacher was lecturing us on safety before class. During the five-minute lecture, we all sat up on the work tables, which had vises on the corners. I wasn't paying much attention to the teacher and started playing with the vise, opening and closing it repeatedly. Suddenly, everyone jumped off the tables and headed to the workstations.

I quickly closed the vise and jumped off the table, not realizing I had clamped my pants to the table. That's when disaster struck. The entire back of my pants ripped off in front of the whole class, and I also smashed my face and wrist into the floor. I don't think this is even the most embarrassing thing to happen to me, but it's definitely in the top 10.

The Most Embarrassing "Oops!" MomentsFlickr, Fabrice Florin

4. Wind On My Wang

I left my apartment one night to go to work. I was half asleep and on auto-pilot to get there. I ran into my neighbor as I was walking to the parking lot. He talked to me for a few seconds, then awkwardly said "bye", grabbed his girlfriend, and walked away. When I got to work, I ran into a co-worker of mine in the parking lot.

He talked to me for a few seconds, then ended the conversation quickly and shuffled away. I took a couple of steps toward the door, the wind blew, and I felt a cool breeze on my wang. My fly was unzipped, and my wangpiece was hanging out of my boxers. Ever since then, I have worn boxer briefs because you can't beat the elastic fly.

The Most Embarrassing "Oops!" MomentsPxhere

5.  Where’s My Mate?

A mate used to pick me up on his way home from his class. We'd go to his place and drink or play games for a few hours, and I'd walk around the corner to go home. One day, I got into his car and said, "Thank God that's over. Let's go home and get…Oh, sorry, wrong car".

An elderly Chinese couple was looking back at me in shock. The car was the same make and model, and the same color, as my friend's. It was also parked in the same place he usually parked. My friend was opposite them, peeing himself laughing at me.

The Most Embarrassing "Oops!" MomentsPexels

6. Out To Lunch

My high school had this bad tradition of becoming rowdy—yelling, throwing food, and so on—when someone walked across the stage in the lunchroom. Usually, unwitting freshmen took the shortcut across the stage rather than walking around the amphitheater-style cafeteria. The overcrowded room would erupt into a spontaneous cacophony of boos and hurled milk containers.

I have no idea how this ever started. While eating lunch one day, a friend noticed a pack of kids starting to amble across the stage. He immediately stood up, yelled, "YOU'RE STUPID", and started booing loudly. Usually, such acts inspired the rest of the mob to join in, but at this moment, it was obvious the guy was alone in his pursuits. Unfortunately, on that day, it was the special ed class committing the transgression.

The Most Embarrassing "Oops!" MomentsPexels

7. All Washed Up

When I was living with my last roommate, we engaged in a campaign of ever-escalating scares and pranks. So, one morning, I snuck into our shared bathroom and stood in the shower, waiting to jump out at him. He always took a shower first thing in the morning, so I didn't think he would be expecting it. I heard him lumber down the hall and step into the bathroom.

I heard him taking a leak, and I prepared myself to jump out as soon as he pulled back the shower curtain, but he didn’t. Then, the sink started running. Getting antsy, I decided to just jump out and scare him from behind. That was a huge mistake.

When I yanked the curtain back, I was surprised to find his girlfriend standing there, washing her crotch with a washcloth. She screamed, and I yelped a pathetic apology and nearly knocked the door off the hinge, trying to get out. I guess she had come over after I went to bed that night, and that's why I didn't know she was in the house.

She was less than happy with me for a few months after that. My roommate, though, thought it was pretty hilarious.

The Most Embarrassing "Oops!" MomentsPexels

8. Falling Short Of My Goal

I was playing summer soccer as a 14–15-year-old at my local park. We were warming up by running around the field a couple of times. This was a football field where the goalposts had supports that allowed us to put a net on and play soccer. As we were running around warming up, I saw some girls I knew at the baseball diamond next to the field.

I was waving, smiling, and generally trying to impress these ladies with my awesome warming-up ability. We happened to be running right behind the goalposts at the time, and I looked away from the girls JUST as I jogged full force directly into the back of a goalpost. It hit me square in the forehead. I was horizontal before I knew what was happening.

My pride got me up and running again in the same short amount of time. I was holding my bleeding head as I continued to run, only to have the girls I knew run after me, screaming after seeing the blood pouring from my head. The rest of the team never let me live that down.

The Most Embarrassing "Oops!" MomentsPexels

9. Caught In The Crosshairs

I was standing in line at Hardee's and struck up a conversation with an 80-year-old lady. I noticed a long, loose hair had fallen onto her face and decided to brush it out of the way. I said, "Let me get that for you", and gently tried to lift the hair off her face. Unfortunately, it was attached to a mole.

The Most Embarrassing "Oops!" MomentsFreepik, mdjaff

10. Nuts To You!

My car was taken in the middle of the night, right outside of my window. I threw my shorts on and called the authorities. Surprisingly, they were there in about five minutes. The officer came in, we sat down, and I started giving my report.

I was perched on the edge of the cushion. I was a bit amped up, so it took me a couple of minutes to realize that the officer was looking anywhere in the room but at me. I looked down, and my nutsack had slipped through a hole in the crotch.

I figured, forget it. I’ve had to deal with their nonsense for years, so it was about time I made one of them uncomfortable. So, I left them swinging until I got up to let him out—he didn't shake my hand.

The Most Embarrassing "Oops!" MomentsPexels

11. Right Was Wrong

I was at a friend's house for the first time ever. I met his dad, shook his hand, etc. About twenty minutes later, I asked, "Hey, where's your bathroom?" My friend told me, "First door on the right". I opened the door only to see something that scarred my eyes.

My friend's dad, sans pants and underwear, was sitting on the bed. He jumped up, ran over to the door, said, "Bathroom's across the hall", and shut the door. Turns out the bathroom door was the first on the left.

The Most Embarrassing "Oops!" MomentsPexels

12. Invasion Of Privacy

Some years ago, my ex and I were camping in a national forest, and on one of our days there, we decided to hike to the top of the mountain to a spring that we'd never been to. It was a very long hike, and we were unprepared. About halfway up the mountain, we ran across a group of people sitting by the side of the trail.

We stopped to ask them if they knew how much farther we had to go. They had no idea, but they were friendly, so we chatted with them for a few minutes while we rested. There was one woman, a little apart from the group, that our dog took a great interest in. He wouldn't leave her alone no matter how much we called him to us.

It became embarrassing, and we had to physically pull him away from her. He was normally really well-behaved, but for some reason, would NOT leave the squatting woman alone. We apologized for the dog's behavior, chatted a minute more, then continued on our way up the mountain.

We were about a mile or two farther when we realized that the woman was apart from the group and the dog wouldn't leave her alone because she was peeing. We had been talking to her and invading her woods-peeing space the whole time.

The Most Embarrassing "Oops!" MomentsPexels

13. Bathing Beauty

I used to do cable installations and would often be at someone's house early; family members would be asleep or getting ready for their day. One morning, I knocked on the door of a nice house. The husband answered, and we discussed what I was supposed to be doing for him.

He let me in and directed me to the bedroom. I was a few steps in front of him, talking about the work I was going to do when I rounded the corner in front of the bedroom. His wife was walking out of the shower with nothing on but a towel on her head and her arms raised, drying her hair.

We saw each other, and both turned around. She apologized profusely, as did I. Obviously, I couldn't just leave because I had a job to do, so I started working in the living room, talking to her husband—who was mildly amused by the whole thing—while she was getting dressed.

After I was done there and she was dressed, I went back into the bedroom where she was. She apologized again and said something to the effect of, "I probably blinded you". I kinda laughed and said, "Nah", but I so badly wanted to tell her how incredibly hot she was and how it was the highlight of my cable career to see her in the buff.

The Most Embarrassing "Oops!" MomentsPexels

14.  Bathroom Humor

I was in the men’s room, answering the call of nature and reading the news on my phone. The article said that “ping”, the social component of iTunes, had been made available on all iPhones the night before. Curiosity got the better of me, and I switched over to iTunes.

Sure enough, there was a “ping” button, and the screen had a section that said, “People Who Follow Me: No one is following you". That struck me as sadly humorous, so I decided to make a screen grab of the message to show my co-workers.

I had to press the menu and power buttons at the same time, at which point, the phone made a clicking noise like a camera. I was in the men’s room, and I wasn’t alone.

The Most Embarrassing "Oops!" MomentsFreepik, pressfoto

15. Sad Slip-Up

I was at a bar and saw a girl I used to hook up with casually. I had heard she was pregnant and assumed she had had the kid already, so I inquired about it.  That turned out to be a tragic mistake. She responded with, "He died. I miscarried. At eight months", then started tearing up and telling me about it and how it wouldn't be so bad if people would just stop asking her about it.

Her fiance was standing behind her shaking his head at me the entire time. A bit later, I saw her run out of the bar crying. The worst part was after I thought about it, I realized I had completely heard that something had gone wrong and they didn't have the kid, it had just totally slipped my mind.

The Most Embarrassing "Oops!" MomentsPexels

16. Bump-ed On A Log

Years ago, right when I had started university, I was walking from one building to another on campus.  Due to their locations, there was a fair length of street running between both. On one of the sidewalks of this street, there was this absolutely humongous tree that had grown deformed. Half of its trunk was nearly horizontal at a VERY low height.

I knew I was running late for a conference I wanted to attend, so I picked up the notebook I had written the time on from my backpack and opened it immediately to see what time it was supposed to start. Less than 10 seconds later, I was on the floor, completely dizzy, and I couldn’t even remember how I got there.

A kind soul helped me up and to campus and told me that I had a bubbling, pulsing lump on my head. They told me that I had smacked into the tree at an almost unnatural speed. By the time I made it home, I had a glorious cartoon-sized bump on my head that lasted for nearly a week before it disappeared.

After the kind passerby picked me up and told me what had happened, the only reaction I had was, "Oh, whoops".

The Most Embarrassing "Oops!" MomentsPxhere

17. I Made A Bad Call

I was in a Barnes and Noble with my cousin. At the checkout, I saw him tossing to himself what I thought was his wallet. In an act of playful aggression, I smacked the wallet out of the air and to the ground hard.

Only after I watched it impact the floor did I realize it was his brand-new iPhone. I felt like a total jerk for the next fifteen minutes and constantly apologized to him.

The Most Embarrassing "Oops!" MomentsPexel

18. Stupidity Never Pays

I worked in human resources for a hospital. An older employee came in seeking my services. While we were talking about our jobs, he asked me what my pay grade was. I told him, and he acted impressed, but I mistook it for him just being nice. I began to talk it down by referring to it as "entry-level".

After he left, I had to go into his records to edit some information and found out that his pay grade is two levels lower than mine. I felt like a complete twit the rest of the day.

The Most Embarrassing "Oops!" MomentsPexels

19. Toddler’s Discovery Time

I was once dating a woman who had two kids. We were sitting in her living room while her children were supposedly in bed. Normally, I avoided women with kids, but she was pretty adamant about not wanting me to be a father to them. We were sitting there watching Netflix when things took an embarrassing turn.

Her two-year-old came walking out the back of the house holding something up and saying, "Ma, what dis?" In his hand was a bright blue vibrator. She went bright red and grabbed it away from him, took him back into his room, and came out a moment later completely flustered and embarrassed.

I waved it off as nothing, we finished the movie, and I went home. After that, she never returned my calls, so I guess the incident was more embarrassing for her than I thought.

The Most Embarrassing "Oops!" MomentsFreepik, cookie_studio

20. Should Have Stayed At Arm’s Length

My buddy was a tattoo artist, and I used to hang out at his tattoo parlor quite often. His piercer was there as usual, and we were hanging out and having a few laughs. The piercer's girlfriend was also there. I had met her a few times but wasn’t that familiar with her.

All of a sudden, I noticed her arms and screamed out, "What happened to your arms?" She had hundreds of scars running up both of her arms from a “bad time" in her life when she used to cut herself. Whoops.

The Most Embarrassing "Oops!" MomentsPexels

21. She Was Fast And Furious

I was in Golden Gate Park on one of the days when they shut down the roads for biking and rollerblading. My friend's sister was wearing rollerblades, and she ended up at the top of a steep slope in the walkway. She was just standing there because she was afraid to come down.

I convinced her to just go for it, and when she finally did, she flew so fast that she slammed right into an old woman walking in the same direction. The old woman landed on top of her, and her wig popped right off her head.

The Most Embarrassing "Oops!" MomentsPexels

22. Fist-Bumping Blunder

I used to work at Home Depot. I had an elderly man in his 70s walk up to me and hold out his fist. I didn't have any idea what he was doing, so I figured he was trying to give me a fist bump. I reluctantly returned him with a fist bump, at which time he just stared at me with the strangest look on his face.

He began to shake his fist, which is when I realized he was trying to hand me a small part he was looking for in the hardware department.

The Most Embarrassing "Oops!" MomentsPexels

23. Mortified Mama

I was loading a new equipment rack into what I thought was an empty classroom. I couldn't see well around it, so I rolled right in to set it up for the company that was coming in the next day to install the equipment. About halfway into the room, I heard a terrified scream and a very strange automated sound. I turned to my side to see a woman pumping for milk.

She looked like she was on the verge of tears. Horrified, I didn't know what to do, so I quickly dumped the rack in the corner, said "sorry", and rushed out. Pretty much everyone in the office has had a good laugh about that one.

The Most Embarrassing "Oops!" MomentsPexels

24. Sinking To New Depths

I had just started a new job working at a factory that produced and packaged industrial chemicals of some sort. On my first day, during lunch, I went to the bathroom to pee. The bathroom had one of those trough-style urinals like you find in sports stadiums.

So, I positioned myself over it and started peeing. About mid-stream, a guy came out of the adjacent stall and gave me a quizzical look. He then walked over next to me and used his foot to press a bar that was located at floor level.  Water started running, and he washed his hands in the large, deep sink that I was currently peeing in.

The Most Embarrassing "Oops!" MomentsPexels

25. She Flipped Her Wig

During a college break, I worked as a teacher's aide at a school for autistic kids. There was this one little guy in my class who always had outbursts and would do crazy, unexpected stuff, so you had to watch your back when he was near. One day, we were sitting around the classroom with the kids, and the unpredictable little guy was sitting next to another aide.

Out of nowhere, the little guy made some loud, unintelligible noise, leaped up, and snatched the wig clear off the aide's head. The now-bald aide grabbed her wig back from the little monster and scurried out of the room.

The Most Embarrassing "Oops!" MomentsFreepik,nakaridore

26. Silence Is Golden

In an old college class—Law and Morality—there was a guy who sat next to me. We were both liberals and would constantly complain about how conservative our instructor was. One day, a guest lecturer who was a doctor came in to talk about why we shouldn't have universal healthcare.

I turned to the guy next to me and said, "Ugh, do you hear this guy and his conservative nonsense? I tuned him out like 10 minutes ago". The guy replied, "Um, that's my dad". I was silent.

The Most Embarrassing "Oops!" MomentsPexels

27. Pile Driver

I worked in retail and was working at the checkouts. A customer dumped all the clothing they wanted to buy on my table, except they were half hanging off the counter. This caused the pile to fall towards the floor.  So, on instinct, I swung my arm to try to catch the items.

Instead of saving the day, I ended up punching an elderly woman in the stomach. Try explaining that to a manager!

The Most Embarrassing "Oops!" MomentsFreepik, stefamerpik

28. Whoa, Radioactive

I was an E3 electronics tech in the Navy, fresh out of school, at my first duty station, which was an airfield. I took the big air search radar out of service for maintenance. There was a safety interlock that prevented it from radiating when it wasn't rotating.

Three of my coworkers were up on the platform, doing their thing in front of the dish, while I was down below in the shelter, checking the electronics with a voltmeter, sig-gens, o-scopes, etc. One part of the procedure I was following required power to be applied to check signal strength in a part of the circuit.

Not thinking, I defeated the interlock and applied power for about 15 seconds, accidentally irradiating some of my co-workers. Two seconds later, my supervisor came down the ladder, wide-eyed, asking me if I was radiating. Seems there was an indicator lamp that lit up on the dish. I just said, “Nope, just doing a check".

The Most Embarrassing "Oops!" MomentsPicryl

29. Holy Jesus, What Did I Do?

I recently moved back to Toronto, and while I was living away, I had dinner at a minister’s house that my aunt and uncle were friends with. The minister had the same name as a good friend of mine from Toronto. Unfortunately, I entered the minister in my phone under the identical name as my friend.

Three months later, when I was back in Toronto, I tried to get a hold of my friend via text. The first text I sent clearly stated that I was back, asking him to come out and meet me at the corner of “Shut Up” and “Shut your mouth".

I wondered why he was not replying, so I checked the number. Suddenly, my blood ran cold. I had sent that to the minister's cell phone. I didn’t hear a reply, but without a doubt, I know he received that text.

The Most Embarrassing "Oops!" MomentsPexels

30. I Didn’t See It Coming

I was playing frisbee with some friends in front of my dorm in college and took off at a full sprint. I had my head turned, watching the frisbee, and I looked forward just in time to run straight into a flag pole and knock myself out. I was wearing sunglasses at the time, which luckily didn't break, but the corner of the sunglasses gouged a huge cut just to the left of my eye socket, and I had to get 21 stitches.

It was really hot, and the classrooms didn't have AC, so a lot of people were having class outside. They could hear the "DING" from across the quad. After that, at parties, girls kept asking me if I was a fighter.

The Most Embarrassing "Oops!" MomentsPexels

31. Suit Up!

When I was a kid, my family and I used to go to this private pool reserved for service personnel. My brother and I were about 10 and 12, respectively, and swimming in the shallow end of the pool. There was a pretty young woman in a two-piece suit with pale white skin talking to what looked like her grandfather.

She raised her hands above her head to give him a poolside hug. The hug turned into a lift as he tried to pull her up and out of the pool. He did it so quickly that her suit bottom slipped down to her knees.

She immediately went into a convulsive shake to get back into the water, but the old man just continued to try to lift her out. It was only a wet behind, but it was a blissful sight that has been indelibly burned into my preteen mind.

The Most Embarrassing "Oops!" MomentsPexels

32. Baring It All

I lived with my “aunt” and “uncle". We're not blood-related in any way, but I had known him my whole life and his wife for the last few years. I got home one day, walked in, sat on the couch, and started reading a magazine. I could hear the shower running. It stopped, and I heard the usual noises of somebody getting ready. All of a sudden, I heard, "TA-DA!!!"

My aunt hadn't realized I was home and ran into the room to show off her newly bare self to who she thought was her husband. I lowered my magazine, yelled, and immediately raised the magazine back up in front of my face as she ran back out of the room. It was extraordinarily awkward for the next few days, but now she makes jokes about it, so I think we're good.

The Most Embarrassing "Oops!" MomentsPexels

33. No More Open Door Policy

When we first moved into our apartment, strangers would regularly walk in the front door daily. I guess the people who lived there before us ran a business or Bible study or something. People were often holding Bibles, and sometimes they had kids with them. My then-boyfriend—now husband—wasn't used to locking the door.

As a result, there were a few awkward moments of being caught in pajamas or eating dinner. One day, we were loud while getting busy in the afternoon and came into the living room to find our door wide open. Someone had left in such a hurry, they neglected to shut the door behind them. We finally got in the habit of always locking the door after that.

The Most Embarrassing "Oops!" MomentsPexels

34. There Is No Fury Like A Woman Scorned

I was working the register at a buffet restaurant during lunch, and it was busy. I had approximately 12–14 people in line and probably 160 diners in the restaurant. I noticed that a couple of guys in line were snickering and trying to get my attention like they were going to do something really funny. I didn’t pay too much attention and proceeded to take care of the next customer in line, who happened to be a full-figured lady.

I asked my usual questions, including, "What would you like to drink today?" To everyone's surprise, one of the guys blurted out in a loud and sophomoric tone, "She NEEDS to have a Diet Coke". At that exact moment, the entire restaurant froze, like in the movies. The guy and his buddy were howling. Everyone turned and looked at them. The lady I was helping turned around and asked, "What did you just say?"

The guys were immediately poker-faced. Then, out of nowhere, another lady, who also happened to be full-figured, walked up to the register and shouted, "I knew when I heard your voice you were going to say something stupid. What is wrong is wrong with you? OOH! You saw my car parked right in front and you thought she was me, didn't you?

“That is why I divorced you. You're an idiot! Apologize to this lady and get out of here". The guy and his buddy apologized and left. Everyone in the restaurant was stunned. The ex-wife also apologized to the lady and even offered to buy her lunch. It was awkward.

The Most Embarrassing "Oops!" MomentsFreepik, 8photo

35. Out Of Sight, Out Of Mind

I'm a lifeguard. On our rotations, we have to walk through the locker rooms to make sure people haven't passed out in there. I worked the morning shift at 5:30 am, and usually, it's just a bunch of old ladies. Some like to use the family changing room, which has a few private rooms and a co-ed locker hallway. The other day, I stumbled upon a shocking sight when one of the older ladies, who was about 70, decided to "forget" that it was co-ed.

She started showering in one of the private rooms but left the door open to the hallway. I was on autopilot and was doing my rotation. I started walking through, heard the shower, and saw the light on. I kind of guessed what was going on, but I was in robot-walking mode and just walked by.

Luckily, I realized what was up in time to walk by the door quickly and keep my head straight. However, I still get fears about what I saw out of the corner of my eye.

The Most Embarrassing "Oops!" MomentsUnsplash, Kenny Eliason

36. The Life Of Brian

One day in my senior year of Lit class, our teacher walked in and asked if anyone knew Brian. Brian was a kid who was conspicuously absent from class that day and was also the most insufferable little jerk I had met up to that point. He made wisecracking comments to teachers that no one found funny and generally could be charitably described as stupid.

So, I, seeing my opportunity at a vicious character snipe, said something snarky along the lines of, "Yeah, but I wish I didn't!" The Lit teacher then said, "Oh, well, Brian broke some ribs yesterday. He was taken to the hospital and was in critical condition, what with his collapsed lung and such. I was just wondering since it seems like he has no friends".

Everyone kind of glanced at me awkwardly, and there was a lot of silence interspersed with throat clearings. I kept my darn mouth closed for the rest of the day. A year or so later, however, I heard he got this life-threatening injury when one of his wrestling teammates beat the snot out of him for mouthing off.

Not sure how true it was, but knowing the guy, it was believable.

The Most Embarrassing "Oops!" MomentsPexels

37. It Was A Rough Ride

After driving about 1,600 kilometers (1,000 miles) one day, I was looking for a place to crash. I pulled into the only motel sporting a “vacancy” sign. Being very fatigued from the drive, I tried to park under an awning.

I didn't pay attention to the height of the awning, though, and totally ripped my mountain bike off the roof of my car, crumpling the Yakima rack, and royally jacking up my bike. I almost cried. To make matters worse, the desk clerk was a jerk, AND they didn't even have a vacant room. I came close to committing battery at that point.

The Most Embarrassing "Oops!" MomentsPxhere

38.  I Suffered Well

I found a co-op through my school that allowed me to travel to different places to install machine equipment. The hotel I was staying at had a Chili's across the parking lot. I called in an order for carry out with the intention of eating it in my hotel room. At that time, I was an avid WoW player and was in the middle of a raid.

During a smoke break, I went to pick up my food from the restaurant. Knowing that I only had a few minutes before everyone was back, I decided to sprint as fast as I could, so I could make it back as soon as possible. After running full speed between two cars and onto a soil parking lot divider, I suddenly saw a fire hydrant directly in my path a few feet ahead.

I sidestepped that obstacle only to see another pipe thing in my way. I tried to quickly sidestep back the other way, but that plan backfired. I lost my footing on the soil right before I got back onto the pavement, and performed a full-speed faceplant right onto the floor. I managed to roll somewhat ninja-like, so other than a skinned knee, I was physically unscathed.

However, I looked around to see if anyone else had seen me, and sure enough, there was a woman sitting in her car a few feet from me, laughing herself silly. My dignity took a severe hit.

The Most Embarrassing "Oops!" MomentsFreepik, wayhomestudio

39.  Time To Go

I was running late for my lecture, so I got dressed as quickly as I could. I ran all the way to the university and burst into the lecture theater, all out of breath. I took a few steps inside and realized that the whole lecture theater—about 100 people—and the lecturer were staring at me. Then, I realized that it wasn’t my class.

I backed away slowly and closed the door. Then, I heard the whole place burst into laughter. It turned out it was the day when all the clocks turned back an hour, so it was actually the middle of the previous lecture. It was extremely embarrassing.

The Most Embarrassing "Oops!" MomentsPexels

40. Need A Lift?

We used to have an outdoor elevator for my elderly grandmother. She had passed, and we were taking her stuff out of her upstairs room that was attached to the outdoor elevator.  I thought, "Let’s just put everything into the elevator". We put a couch, a loveseat, a recliner, two bookshelves, a desk, and a bed, and I pressed the down button. I didn’t notice the “300 lb max” sign. The elevator fell and crashed.

The Most Embarrassing "Oops!" MomentsFreepik, 8photo

41. Down In The Dump-ster

I ordered a pizza for myself and my mother at her apartment. I was asked to take the recycling out, which involved dumping it down a chute that went into a gigantic bin some floors down. At the time, there was a huge pile full of cardboard, papers, etc. When I came back into the room ready to eat the pizza, I was told that the pizza was on the counter in the cardboard box.

There was no box on the counter. I had just thrown it down 20 flights of stairs to its doom.

The Most Embarrassing "Oops!" MomentsThe Most Embarrassing "Oops!" MomentsThe Most Embarrassing "Oops!" MomentsThe Most Embarrassing "Oops!" MomentsFlickr, A National Acrobat

42. A Wench In Need Of Water

I must have been 14 or so when I went to a Renaissance fair with my friend and father. It was an extremely hot summer day, and I was all dressed up—bodice, long skirt, hat, the works. I realized I was getting thirsty from being out in the sun, so I told my friend I'd be right back and that I was just going to get a bottle of water from one of the vendors.

The line was extremely long, but I needed that water, so I waited for at least 10 minutes in line, burning up. That turned out to be a big mistake. When FINALLY it was my turn, I started to dream. When I woke up, I was on the ground with a group of pirates and wenches around me.

I could barely talk—I was dehydrated and miserable. I was led to the big tent where all the actors got dressed and I got the star treatment from the fire breathers and clowns. I got water and food, and it was pretty cool all in all, even if I had passed out in front of everyone.

The Most Embarrassing "Oops!" MomentsWikimedia Commons, aimee daniells

43. I Needed To Book

I had just moved into my first-ever apartment away from home. I had just woken up, was running a little late, hurrying to catch the university transit to campus, and was totally out of it. I realized I had forgotten my books, so I turned back and saw someone who looked vaguely like one of my roommates leaving an apartment.

I walked in, and the dude was like, "What are you doing?" I told him, "Forgot something", to which he replied, "In my apartment?" I did a double take and realized I was in the wrong apartment. I shamefully ran away, despite my apartment being exactly diagonal to that one. My books weren't worth that guy knowing I was his neighbor.

The Most Embarrassing "Oops!" MomentsPexels

44. Dripping With Guilt

I was driving down the street during spring, and there was melted, dirty slush everywhere. I was just about at McDonald’s, and right before I turned into the parking lot, there was a puddle. A pedestrian came out of nowhere, and I completely soaked this lady.

I felt terrible. I went inside and got in line. Right behind me was the lady, completely dripping wet. I didn't know if she recognized me, but my actions once I saw her probably gave it away.

The Most Embarrassing "Oops!" MomentsPexels

45. The Girls Were Sprung

When I was in Grade 9, we had to wait in the gym until the bell rang to exit the class. The gym mats were still on the floor, and my friend did a front handspring on the mat. Since we were waiting for the bell to go and I had nothing to do, I decided to do one as well.

Except when I was midway through it, someone held my legs, so I couldn’t complete it and was left upside down. Since I was upside down, my shirt came off, and everyone could see my training bra. That was not a good day.

The Most Embarrassing "Oops!" MomentsPexels

46. It Was No Walk In The Park

I had an awful stomach bug that came out of nowhere while walking my dog. Diarrhea struck fast. I had to go poo on my neighbor’s lawn beside a bush.  It was the middle of the day, so a few people saw it, and my wife knew before I even got to wipe myself.

For around 48 hours, I genuinely thought I wasn’t going to make it. Luckily, I’m not easily embarrassed and my stance on it was, “I can’t hold what’s not in my hand". However, my neighbor and I still aren’t on speaking terms.

The Most Embarrassing "Oops!" MomentsFreepik, teksomolika

47. Seizing The Day

While riding a bike down a rural city street, I took a shortcut through the bus station. Out of the corner of my eye, I caught sight of a woman having an epileptic seizure. The woman was on a bus stop bench, but it disappeared out of my line of sight as soon as my brain started to process the scene. My first impression was that she looked mentally disabled, and after about 10 seconds, it occurred to me to circle back and check if everything was alright.

Coming around the building from the opposite side, I spotted the woman again. She was still shaking and flailing, and I noticed she was being helped or restrained by a young man. My mind switched gears and started thinking of the possibility of an attack, but the woman was sitting in the person’s lap, and he couldn’t have been more than 15 years old.

Clearly, this woman needed help. So, seconds later, I rode up to the bench from behind and started to say, "Is everything OK" when I noticed the woman's pants were at her knees and the boy was knuckles deep in her hooha. The woman stopped shaking and flailing about as I began my getaway-o-shame. I still remember the look on their faces.

The Most Embarrassing "Oops!" MomentsPexels

48. Hot For Teacher

My high school English teacher hired a couple of my buddies and me to help him and his hot wife move. It was only his second year teaching, so they were only in their mid-20s. We attempted to move his bedroom dresser, but it was heavy, so we began removing drawers to lighten the load. The very first drawer we opened was full of adult toys.

There were vibrators, plugs, beads, lube, and Polaroids of his wife, completely in the buff, in various positions using the toys. He walked in a few seconds after we found it and turned beet red. The only thing he could mutter was, "You weren't supposed to see that".

The Most Embarrassing "Oops!" MomentsPexels

49. Caught Red-Handed

There was a garden outside my house in college and no one knew who it belonged to. So, I, being completely broke, would take vegetables from it periodically. One day, the owner caught me with an armful of peppers and banana squash. He said, "Oh, heck no, man".  I said nothing and proceeded to extend them out to him as if presenting a gift.

The Most Embarrassing "Oops!" MomentsPexels

50. Fast Friend Freak Out

I was young and staying in a backpacker campground/halfway house for people who were down on their luck. There was a young guy around my age who eagerly introduced himself, then followed me everywhere like I was his new best friend. I didn't know anyone, so I tolerated it politely, but it started getting a bit creepy.

I left my door open and went to the bathroom. When I came back, he had set up a TV and a stereo in my room. He said it was a spare and that he was getting his parents to buy him a better set, so he wanted his mate—me—to look after it for him. I thanked him, tried to say it wasn't necessary, but finally caved and accepted it.

I kept thinking it WOULD be nice, but it still felt weird. Later that day, some girl who I'd come to know a little asked me how it was going with my new best friend and gave me a knowing smile. I said it was weird that I had barely met this guy, and he was suddenly coming into my room uninvited, giving me gifts, and calling me his mate.

I told her I should probably move on and sell it to teach him not to be so trusting. She laughed and said, "Yeah, what do you really think of him, though?" I replied, "I dunno. He’s a nice guy, but a bit weird. Is he like a special ed kid or something?"  She burst out cackling, then the guy said from behind her, "Thanks, mate, I'll be over to pick up my stuff later!"

The Most Embarrassing "Oops!" MomentsPexels

 

Sources:


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