31 of the Most Awkward Situations People Have Been in With a Stranger

For instance: Being drunkenly handcuffed together
31 of the Most Awkward Situations People Have Been in With a Stranger

Any encounter you have with a stranger has the potential to be awkward, no matter how brief the interaction is. However, it’s probably best to be in a hauntingly cringeworthy situation with a guest star in your life rather than a recurring cast member — after all, you’ll likely never have to see that guest star again, while a main cast member you’re pretty much stuck with forever. 

Redditors got open and honest about the awkward encounters they’ve had with people they pray they’ll never see again, and they’ve mostly embraced the humiliation by laughing at themselves. We’re incredibly grateful for that, because one person’s gaffe when asking a Toys ‘R’ Us clerk for a “large Woody” is a story that absolutely needs to be shared.

paypermon . 4y Got on an elevator with a woman and she had on these really nice boots so I complimented them by saying nice boots she cups her breasts and says well you're not shy,thank you they're real and then immediately realized I said booTs ,she thought I said nice boobs longest elevator ride ever. To this day whenever I say boots in any context I do so with a very hard deliberate T
realmcphearson . 4y I had just pulled into a parking spot at the mall and saw my friend and his girlfriend pull in a few spaces past mine. Thinking it would be funny, I snuck up to their car and started slapping their window like a crazy person. It was not my friends in that car. I still cringe years later remembering the look of pure terror on that poor girls face. ... 225
cfcnotbummer . 4y Discovered, whilst at the top of StPauls cathedral, that I am terrified of heights. A Norwegian woman was having the same experience. We were so unnerved we ended up holding one another and bumping down the spiral staircase on our backsides. Parted ways at the bottom without a word or a backward glance. ... 6k
buefordbaxter . 4y My wife and I went out for a drink one night. We walk into the bar, I see someone I know at the bar with their back turned, walk up behind them and tickled their sides. Turned out I didn't know this person, they just gave me a weird look and walked away. Got their spot at the bar though ... 22.1k
immathrowaway456 . 4y In the cinema. I interlocked my fingers with the kid sitting beside me for a full minute. Turns out, he wasn't my kid. ... 49.3k
JavaOrlando 4y I worked security at an aquatic theme park and was watching Jeopardy in the employee entrance. One of the veterinarians came through and watched it with me for a bit. Не said he watches it religiously and he'd passed the test for the show and was hoping to get selected. He'd heard that they like to have a diverse group of contestants, and they hadn't had a black guy for a while, so he liked his chances. A few days later, there are two black contestants, so when I see him leaving the next time I say, hey,
 4y I went for a bike ride in my neighborhood at about 12 at night a month ago. It was pitch black other than streetlights every 5 or 6 houses. I was kinda just zoning out, enjoying the fresh air, when something moved out of the corner of my eye. I turned my head to look, and I immediately assumed it was some kind of monster (I had just finished a horror movie), so I let out an extremely loud, bloodcurdling scream in the middle of the night in a silent suburban neighborhood. The thing, which turned out to
dustinrosenfeld . 4y When I was little, I was at a museum and saw a man that I thought was my dad. I ran up behind him and hugged his legs. Was not my dad. Не flinched and kicked his leg back. I stumbled back and just sat down and cried in the middle of the floor. Then it occurred to me that I'd come to the museum with my mom. ... 851
cloketre 4y I worked the entrance gate for a theme park. Our season pass holders used a biometric scan of their right index finger to verify their identity. One day a little girl walks up with her family, who only spoke Spanish, scans her pass and places her left finger on the scanner. I say, Can you use your right finger sweetie? Then, her mother raises the girls right arm to show me she doesn't actually have a right hand. Seemed to be due to a birth defect rather than a horrific accident. However, her left finger keeps getting rejected,
TheWanderingWriter 4y I used to do security work at parties. One night there was an alert call for a young woman gone missing. I found her with her dress hitched up looking for her underwear in the bushes. I managed to unlock her phone to call her dad, who from his name I recognised as the district attorney. Не comes over to pick up his intoxicated daughter. While I was carrying her to the car she was making very sexual remarks about me carrying her, all the while her father is hearing me out like I was responsible for his
Kaneland96 4y It was my first time voting in a presidential election in 2016 since becoming old enough to do so, and polling place was at a library. When I get to the front of the line and start filling out the required papers, I mention it's my first time and what to do next. After hearing this, the women who was working there and helping me raised her voice and said Hey everyone, we've got a first time voter here! and started clapping so they all would clap as well. Nobody clapped, and I was just standing there really
 . 4y Hooked up with a guy in college and fell asleep in his dorm room. I woke up in the middle of the night needing to pee so fucking badly but unable to find any of my clothes right away. I ended up spending so long trying to find them in the dark that by the time I had enough to wear out in the hall to get to the bathroom I didn't think I'd make it. Не was still sleeping so I grabbed a big reusable water bottle and squatted over it. It was blissful relief until
 4y Handcuffed to eachother while drunk. No i don't know where the handcuffs came from. And no i didnt know who it was. ... 68
 . 4y Woke up from a blackout drunk in bed with a woman I had never seen before. I didn't know her name or anything about her. Decided to try and get her name off her drivers license before she woke up. She woke to find me digging through her purse. ... 24.8k
SimpleWayfarer . 4 4y I walked into a blind student at my school (by accident, of course). We tangoed on the sidewalk for a minute before he finally pushed me away and kept walking, leaving me speechless as to what the hell just happened. ... 47
avtomat_kosmonavta . 4y I tried to make some moves on a girl when I was in high school. We were in a 7/11 near the back, and because of the late hour, I figured we were alone. When she turned me down and left, I decided to drown my sorrows with a bag of Sour Patch Kids and physically ran into the older, bearded man who had been buying nuts. Не gave me a sympathetic look and opened his mouth as if to say something, and I panicked. I said, see you tomorrow! and left the store. I still think about
ballsagna2time . 4y At an art studio in LA, my girlfriend was wearing a denim jacket As we looked at a piece together, out of the corner of my eye I saw the jacket and I reach over to grab her butt. A sudden Oh! Comes from beside me and a woman 30 years older than me is standing there blushing. I tell her I thought she was someone else and run away to my girlfriend. A few minutes later the lady comes and finds us to talk about young love and how cute we are while making too much
firstblindmouse 4y When I was a teenager my friends and I would spend the weekends staying up late playing video games and eating junk food. I was also a cross country runner, and on this particular night I was experiencing some extreme chafing from a long run earlier that day. While we were at the gas station getting Doritos and energy drinks I announced to who I thought was my friend, Man, my nipples really hurt. Upon realizing it was a complete stranger with whom I had just shared this intimate detail I simply stared at him and said You're
StarbugRedDwarf . 4y My son had small Toy Story figurines but wanted big ones for Christmas. I walked into Toy R Us and asked the male clerk, Do you have a large Woody? Не turned bright red, I wheeled around and marched out and didn't go back for months. ... 5k
DropsyDropsy 4y Worked at a hotel front desk 3rd shift and an old, maybe 75+ lady, called the front desk and wanted a pillow delivered to her room. I took the pillow. when I got there she wanted me to come inside. I'm like uhhh naw here is your pillow, she insisted so I did. I get inside she shuts the door and tells me to put the pillow on the bed. She then goes to a drawer in her dresser, at this time I'm like I need to return to the front desk, thinking the worst. She then pulls
craftznquiltz 4y The most awkward moment of my life thus far was with a stranger. I was in Quebec airport going through customs with my family. Because of some recent changes to their system they didn't have everyone in a line, but instead in a large pen where they would release ~50 people at a time (chaos). When my family is at the front, they release us and everyone is running forward in a mass trying to get to the kiosks. Next to me is a tall Swedish man trying to get his family a kiosk, he is running forward
 4y I worked at Old Navy and some lady was looking at mens shirts and she stopped me and held up this shirt and asked if I thought it would fit her son. I looked around and no one else was around. We stood in silence for maybe 30 seconds before she started laughing and said Oh! Haha, you dont know my son he lives in Michigan (we were in Washington State)... Nevermind me, I'm just stoned! Haha... And then she went and bought the shirt. ... 17k
mronion82 . 4y Not long ago I incorporated a short visit to the local supermarket into my usual dog walk. The dog was tied up outside, and as I was crouched down to unclip him a woman came out of the shop and fell over me. For a few brief seconds I was in the middle of a dog/old woman humping sandwich. We're British though, so everyone looked embarrassed and we both said sorry. ... 2.4k
rbeks 4y One time I was in middle school and someone parked right in front of our mailbox. Now the annoying thing about that is that at my house they could hav pulled either 10 feet forward or backwards and would have not been right in front of our mailbox. So me being an annoying middle schooler went out to get the mail and also walked up to the car yelling ugh why do people always park right in front of our mailbox when there are other perfectly good places to park!! And as I was doing that I made
jldavidson321 . 4y When I was in college, I was waiting for a shuttle bus, and a girl I had previously been in a class with walks up to the stop with a guy I don't know. I say Hi, how are you and we have a short exchange of pleasantries, and then she turns to the guy next to her and in sign language says  I don't remember her name So I sign That's ok, I don't remember your name either and offer my hand to the guy with her and introduce myself. ... 2.6k
Bearingstraight . 4y One time I was in a two story dicks sporting goods and after going up the escalator I made a right and started walking. Out of the corner of my eye I saw a shirt, really cool design and fabric. I stopped and looked at the spot I saw and started feeling the fabric to see how warm it would be, ripping, etc. Well all the sudden I hear, dude. What're you doing I look up and it wasn't a mannequin. It was a man. My eyes grew wide and I fled. Left the mall even. ...
campariferrari 4y I was in the backseat of a Lyft line with a stranger next to me. I was texting a friend about music and TI's dick pic came up. If you've never seen it, it's so weird and terrible, look it up. Anyway, I was explaining that via text to said friend and of course I couldn't leave him hanging. Trying to discreetly Google, screenshot, and send a celebrity dick pic is bad enough, but respectably sitting next to a stranger. I tried to angle my phone away from her, but it was dark outside so she could still
sallyapple7 . 4y Disney's Tower of Terror. 12 year old me spent the entire lineup desperately trying to catch the attention of a cute guy who was there with his dad. Ended up sitting in the same car as him on the ride. As the ride starts I grab my mom's hand for support. Near the end I realised that my mom was on the other side of me and I'd been holding hands with the cute guy's dad the entire time. They were all laughing at me. ... 588
Pannycakes666 . 4y Switched colleges and needed a new weed guy. Got recommended a friend of a friend. I went over to his place to pick up and he was just butt ass naked with his ferret acting like nothing was out of the ordinary. Pretty good bud. ... 220
Dried_Squid_.. 4y Had to use a public restroom and the guy in the stall next to me forgot to lower the volume (or put his headphones in) and I heard the jingle from a very specific company that makes animated adult entertainment. The person quickly made sure the video was no longer audible for me but it was too late I knew what he was gonna do. I don't think he knew that I knew what he was watching but to have to sit there waiting for my body to clean itself out while knowing that he's watching animated porn
iamsoveryverytired 4y 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
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