awkward situation

People Are Sharing The Most Awkward Situation They’ve Ever Been In & It’ll Make You Cringe

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Everyone has one: a moment where you did something incredibly stupid or awkward and it’s burned into your memory for the rest of time.

No, seriously, you may go days, weeks, maybe even YEARS without thinking about it, but then one night as you’re trying to go to sleep your stupid brain goes, “lmao remember when you called Mr Black ‘dad’ in Year Two?”


Recently on Reddit, someone asked users the most awkward situation they’ve ever been in and it quickly started trending. Here are some of the best answers.

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1. The bad slap

“When I was a kid, we were on holiday and decided to go to church. While we were there I decided that it would be funny if I slapped my dad’s ass with both hands. So I ran in full speed to maximize the impact of the slap. I ended up slapping a stranger who also happened to walk next to a woman with a stroller in his hands which made me think it was my dad. It was even worse that my parents saw it as well.” – beach_or_bitch 

2. The ill-timed prank

“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.” – RobboBanano

3. The wrong girl

“When I was in high school with my girlfriend at the time and her family at the mall shopping. Walking around the store we all get separated and I was all alone. I wandered around until I saw the back of my girlfriend.

I sneak up behind her, grab her butt and reach around and grab her boob. She screams, turns around and it’s her mum. We stared at each other for a second and she laughed. I immediately turn red and run away. I was so embarrassed, I had to leave. I couldn’t be around my girlfriend’s mother for two months, I was so embarrassed. In my defence, they had very similar physiques.” – jinkinater

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4. The repair gone wrong

“While my dad was out of the country there was a major leak from the water tank in the loft which caused serious damage to the property and caused lots of other issues, including a hole in the ceiling. I called out a repair guy only to hear a huge “boom”, followed by a string of expletives before he called for help. I found him half in a cupboard, soaking wet, with his hand on a burst water pipe.

I ended up having to help. This involved me climbing up to the loft (in a short dress and stockings while he was basically laid on the floor underneath the ladder) and trying to turn off the water from there. This didn’t work so we ended up switching places so he could professionally investigate. Swapping places involved me getting soaking wet, and having to press up against the guy and contort myself into position in order to minimise the risk of further damage and water explosively spraying everywhere.

The situation was like a bad porn parody.” – brokenstar64

5. The accidental well wishes

“I was with my mum buying flowers at a florist for a New Year’s eve party. The florist was obviously a very lonely woman and wouldn’t stop going on about how she isn’t doing anything for New Year’s and how it’s so nice we have friends to visit, to the point where it became really saddening. My mother obviously really felt for her.

Every now and again, maybe twice a year, she has a brain fart and accidentally says what she is thinking. That day was one of those rare days. After paying for the flowers, my mum said ‘thanks! Hope you find a friend soon!’. I look at her in shock, the woman looks at her in shock, and my mum just gasps, apologises and literally backs out of the store. God, it was so awkward.” – iamsoveryverytired

 6. The traumatising nude

“I was looking at my mother’s 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 shit.” – Throbbingprepuce

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7. And the reverse situation

“Reverse happened to me. I was showing my mom a picture on my phone while I was holding it, she takes it and even though I express the fact that there’s only one pic of what I wanted to show her so she wouldn’t swipe, she did anyway and ended up seeing one of my nudes.” – FineAliReadIt

8. The wrong bowling balls

“My SO and I like to go bowling with a group of his coworkers and their SO’s. The very first time we went I was walking back to the group after using the bathroom and noticed it was my turn. I also noticed my SO was standing beside one of his coworkers both with their backs to me. They are of similar stature and had on similar clothes. So I walked by and confidently squeezed the ass of my SO (I thought).

I finished bowling and came back to his coworker with the most stunned expression on his face, and my SO doubled over laughing. Luckily the coworker and his wife are super cool and thought it was hilarious. Now every time I drop by SO’s work to visit, his coworker asks if I’m here to grab his ass again.” – Rygard

9. The sexting gone wrong

“I was on a road trip (passenger) and sexting with my girlfriend. During the steamy conversation I got a text saying “Please stop somewhere and get some sleep tonight, don’t try to do the whole trip in one day”. I assumed it was another text from my girlfriend, so I replied, “well judging from how horny you made me, I don’t know if I’ll be able to sleep”. It was my mother.”  – Phil_Drill

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10. The unlocked door mishap

On the way to a conference on the train. Nature called, so off I went to the onboard toilet. Hit the open button, door starts its long, slow opening and greeted with the screams of a woman in full pants down squat who forgot to lock the door. Being British, I apologise, hit the close button and wait outside, avoiding eye contact when the woman exits.

Fast forward 2 hours, I am front row for one of the conference talks and who should take the stage? Yup. – sockhead99

11. The gas attack

“I was at Disney World with my parents when I was younger. We were in a store just wandering around and my dad is a gassy guy. He can rip one anytime anywhere. He sees a woman that looks like my mom from behind so he ambled over to her, let’s one rip and says “how do you like THAT.”

The lady turned around and it wasn’t my mom, she standing a few feet away laughing her ass off cause she knew what he did. He mumbled an apology to the lady and took off. We never let him live it down.” – Deleted User 

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