June 19, 2023 | Samuel Ira

People Share The Most Awkward Situation They've Ever Been In With A Stranger

Meeting new people is an inevitable part of life. On a single day, you could meet dozens of people you've never seen or spoken to before. With all these occurrences, the likelihood of being stuck in an awkward situation with a stranger is naturally high.

Some people even have nightmares of just such instances occurring. Well, the people from this list have lived those nightmares. They were trapped in an awkward situation with a person they didn't know, and it was traumatizing for them. Here are their cringy and frightening stories.


Don't forget to check the comment section below the article for more interesting stories!

#1 Birth Stranger

I was adopted at birth. I learned who my birth family was in when I was in my early 30s. I met one of my sisters, but nobody else yet.

My sister told me that our grandpa was going to be taken off life support and that he wanted to talk to me before he died. We traveled to the hospital, which was several hours away. We met our mom in the hospital lobby for the first time ever, then went into grandpa’s room together. All of our family members were there to say their goodbyes.

Probably only 5% of them knew of my existence. Suddenly, all the attention was on me, the stranger. They had me kneel by his side as he apologized through tears for pressuring my mom, who I just met, to give me away for adoption years ago. People looked pretty shocked. The experience flooded me with a thousand emotions, and awkward was definitely in there somewhere.


#2 Whoppers, You Know What I Mean?

I was at a wedding reception and went to use the bathroom. I was standing at the urinal when a guy came up to me. He then let out giant flatulence.

“Oof, check out the smell of this! Whew! You gotta let ‘em out here and not by those girls, you know?”

And I just go “Ha! Yep," and walk out. I felt very uncomfortable.


#3 No Right Way To Do This

I worked at the entrance gate to a theme park. We used a biometric scanner to verify the identities of our season pass holders. They would scan their pass, then scan their right index finger to get in.

One day, a little girl walked up with her family, who only spoke Spanish. She scanned her pass and then placed her left finger on the scanner. I asked her, “Could you use your right finger sweetie?” Then, her mother raised the girl's right arm to show me she didn’t have a right hand. Seemed to be due to a birth defect rather than a horrific accident.


#4 Blond Monster

I went for a bike ride in my neighborhood at about 12 a.m. It was pitch black other than a couple of streetlights that were lit every 5 or 6 houses.

I was kind of just zoning out, enjoying the fresh air, when something moved in the corner of my eye. I turned my head to look, and I immediately assumed it was some kind of monster. I let out an extremely loud, bloodcurdling scream in the middle of the night in a silent suburban neighborhood. The mysterious figure turned out to be a blond soccer mom, who screamed right back at me.

I zipped past her on my bike, yelling, "Oh my god I'm so sorry!" over and over again until I got off the street.



#5 Need Another Nurse

I'm a pediatric nurse, but we “float” to other floors when we have more nurses than we need. One time, I was sent to an adult floor to work as an assistant since theirs had called in sick. An older male patient called out asking for help to get up to the bathroom. He stood, tried to pivot, and his newly operated knee gave out. All 320 pounds of him came down on top of me and we laid there for almost an hour. I had closed the door for privacy, and neither he nor I could yell loud enough to get anyone's attention.

My phone was 10 feet from me on the floor after it fell out of my scrubs and it rang incessantly. Finally, the other assistant came to find me. The patient was fine since he fell on me, but I was sore for a week. We were nose to nose the whole time and boy was it awkward.


#6 Terror Shared

I discovered, whilst at the top of St Paul's 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. We parted ways at the bottom without a word or a backward glance.


#7 Canine Resemblance

One time, I was at a dog groomer's to pick up my dog. He's fairly small and white. Usually, he just gets a short trim, so that's what I always expect to see.

I walked up to the counter and requested for my dog. The clerk told me he'd be out in a moment. 30 seconds later, an attendant walked out to the lobby from the back door with a dog that immediately ran to me.

"Hey, buddy!" I said as I walked up and attempted to pick up him. Instead of jumping into my arms, he started recoiling back and gave me a nip. An old man behind me then asked, "Hey, is that your dog?" Thinking that was a pretty weird question, I responded, "Yep!"

At that point, he said, "I don't think so mister, that's my dog." When I took a closer look, I realized the dog looked exactly like mine after grooming. My face went completely red and the whole lobby started laughing.


#8 Accidental Alarm

On the first day of my new job, I was in the elevator going up five floors. As the doors were closing, a girl barged through and thumped her backpack down.

This set off the assault alarm in the external pocket of her bag. So awkward.


#9 Bad Parody

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, including a hole in the ceiling.

I called a repair guy. While he was working on the leak, I heard 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 to minimize the risk of further damage.



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#10 A Strange Thanks

I serve in the Air Force. One time, I got injured at work and had to go to the hospital. Nothing serious; I just dinged my finger super hard ( and messed up the ligament).

When I got to the hospital, I walked through the front door, still in uniform. Some nice older man came up to me and thanked me for my service. I told him I appreciated his support, and then he abruptly asked me if I was married.

As soon as I told him no, he turned to a random woman walking by and said something along the lines of: "See this nice man? You should go on a date with him!" At first, I thought maybe he knew the woman, but by the shocked look on her face, I could easily tell he did NOT know her. She stopped for a moment and he asked her again... She just went wide-eyed, kind of stuttered for a moment and then bee-lined it for the door.

I really didn't know what to say.



#11 Awkwardly Loud Thought

I was with my mom 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 wasn’t doing anything for New Year’s. My mother really felt for her.

One thing to know about my mom is that every now and again, she has a tactless episode and accidentally says what she is thinking out loud. That day was one of those rare days.

After paying for the flowers, my mom said, "Thanks! Hope you find a friend soon!" I looked at her in shock, and my mom gasped. She apologized immediately and literally backed out of the store.

It was so awkward.


#12 Denver Adventure

In Denver, Colorado, I met some man with a giant suitcase full of stolen clothes and a ripped backpack that he asked me to carry. We stopped to take a break because the suitcase was like, 100 pounds. Then, he told me to check out what was in the backpack. I unzipped it to find a bunch of over-the-counter pills and a bag of other unknown substances. When h asked me if I wanted to try some, I just gave him his bag back and went away.


#13 Lock The Door!

My girlfriend and I were eating with some friends and  I needed to go to the bathroom. It was open, so I walked right on in.

The room was pretty big, with a urinal and sink on one side, and a toilet on the opposite side. There was a guy in at the urinal and he gave me a REALLY strange look when I walked in. I went on over to the toilet, went #1, then totally realized I was in a SINGLE PERSON BATHROOM.

By that point, the guy had hastily run out after finishing his business. I took care of my own affairs and had to do the walk of shame past him as I walked back to my table. I told my significant other later that night and she thought it was hilarious.


#14 Accidentally Personal

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 her jacket and reached over to grab her. A sudden "Oh!" could be heard from beside me and a woman 30 years older than me was just standing there, blushing. I told her I thought she was someone else, then ran away to my girlfriend. A few minutes later, the lady found us to talk about young love and how cute we were together.


#15 Size Matters

My son had small Toy Story figurines but wanted big ones for Christmas. I walked into Toys R Us and asked the male clerk, "Do you have a large Woody?"

He turned bright red.

I wheeled around, marched out and didn't go back for months.


#16 Not A Carjacking, I Swear

One time, I was in a parking lot waiting to get into my friend’s dad’s car. I saw a car that looked identical to the one I needed to get into, so I got into it.

It turned out, it was not the car I was supposed to be in. The stranger's expression of pure fear still pops into my head from time to time.



#17 Very Realistic

This happened to me in Japan. I was in a clothing store and my wife was shopping. Being the dutiful husband that I am, I remained silent and stayed out of the way, barely moving a muscle.

A little girl, maybe 4 years old, approached from one side and slipped her hand into mine.

I looked down. She must've thought "Wow, this mannequin's hand is warm." Then it clicked.

She looked up at me with such a look of terror... In a flash, she was gone, and I hope she will forever remember with terror the amused sparkle in my eyes.


#18 Running Hazard

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 I took 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 pecs 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 not my friend” and walked away. I didn’t go back to that gas station for a long time.


#19 One Way To Steal A Seat

My wife and I went out for a drink one night. We walked into the bar and I immediately saw someone I knew. I walked up behind him and tickled his sides. It turned out, I didn't know this person. He just gave me a weird look and walked away. We got his spot at the bar though.


#20 The Window Slapper

I had just pulled into a parking spot at the mall. I 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 turned out, it was not them in that car.

I still cringe years later remembering the look of pure terror on that poor girl's face.


#21 Making Contact

I was at a bar with my brother's old phone. A random girl asked me if she could use my phone to call her own because she had lost it. She began dialing her number and bam, right there on the screen is her name saved on my phone. My brother's contacts must have transferred when I took his phone. Her eyes got real big and she looked up at me with what could only be described as confused fear! I tried to ask her if she knew my brother, to which she said she did, but she was obviously still weirded out. She deleted her number from the phone and fled so fast.


#22 Father And Son

We were lining up for 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. I ended up sitting in the same car as him on the ride. As the ride started, I grabbed my mom's hand for support. Near the end, I realized 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.



#23 Not In My Eye

I was at a bar with some friends watching a basketball game, and this guy kept asking me to check out his girlfriend every time she went away.

For example, when she got up to go outside for some air, he stayed in and was like: “Be honest, is that not the best butt you’ve ever seen?”

He did this several times. I felt so uncomfortable, and there’s no nice way of putting it — she wasn’t attractive whatsoever to me.

I’m glad that guy is happy with her, though.


#24 A Sad Patch

My boyfriend and I were with another friend and we were walking home from a movie. We came across a guy sitting in a small patch of grass rocking back and forth. My boyfriend wanted to keep walking, but I felt the need to ask if he was okay. He immediately broke down and said he wanted to end it all. It turned into a really awkward situation because the other two didn't know what to do.

We ended up sitting with him for a while as he broke down, and we called emergency services because he was apparently very far from home. He eventually calmed down enough and we drove him to the hospital. He was very thankful once he was there and safe. I still think about him every time I walk past that patch of grass, I really hope he is okay.


#25 Something To Celebrate

It was my first time voting in a presidential election and my polling place was at a library. When I got to the front of the line and started filling out the required papers, I mentioned that it was my first time and asked what to do next. After hearing this, the woman who was working there raised her voice and said “Hey everyone, we’ve got a first-time voter here!” She started clapping so they would all clap as well. Nobody clapped, and I was just standing there really embarrassed before quietly saying, “Can I just go vote now?”


#26 Pizza-dental

During my first week at college as a freshman, I wandered into the cafeteria, still unsure of how things worked.

I spotted a pizza station and waited in line. I grabbed a slice of pizza with the pizza slice grabber, but the scalding hot pizza slid off and landed face down on the cute girl’s foot behind me. Sauce and hot cheese explode everywhere up her leg. And since it was the end of summer, she was wearing sandals.

In a panic, I muttered “I’m so sorry,” and ran out of the cafeteria without eating for the rest of the day.


#27 Made Sense In The Moment

I worked at Old Navy and some lady was looking at men's shirts. She stopped me and held up a shirt to me, asking if I thought it would fit her son. I looked around and no one else was there. We stood in silence for maybe 30 seconds before she started laughing and said, "Oh! Haha, you don't know my son; he lives in Michigan. Nevermind me! Haha." And then she went and bought it.


#28 Needed His Eyes Checked

On a trip to Orlando, my husband, son, and I spent some time in the swimming pool at our hotel. There was a large family enjoying a family reunion at the hotel that week as well. They were a super nice family! We were all kind of hanging out together and our kids were playing.

Well, imagine my surprise when I watched my husband swim into the shallow end and wrap his arms around a woman standing there. He burst out of the water and said, "Oh, you're not my wife!" to the 50-something lady. She said, "I could be!"

He has since had Lasik!


#29 Married A Winner

A woman at a gas station didn't know how to put air in her tires, so I helped her. She called her husband on speaker phone to let him know she found some nice man to help her. Then, I heard him call her an idiot and say that I was only helping her because I wanted to get together with her.

She stammered and tried to explain that nothing was going on between us. After she got off the phone, she looked at me as if her husband just caught her cheating. No thank you; nothing. And for some reason, I felt guilty for even helping her out.


#30 Awkward Sandwich

Not long ago, I made a short visit to the local supermarket on my usual dog walk. My 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 sandwiched between my dog and an old woman. We're British though, so everyone looked embarrassed and we both said sorry.


#31 Perfect Alignment Amidst Chaos

The most awkward moment of my life thus far was with a stranger. I was in a 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 around 50 people at a time.

When my family got to the front, they released us and everyone was running forward in a mass, trying to get to the kiosks. Next to me was a tall Swedish man trying to get his family a kiosk; he was running forward and waving his arm behind him in a “come on” motion, clearly frantic. Well, somehow his middle and pointer fingers went perfectly into my two nose holes.

As he then ripped his arm upwards to motion his family forward, my nose was also ripped forward, and I immediately began bleeding everywhere. He looked at me in horror, and the customs agents looked at me in bewilderment. The language barriers made the situation all the more awkward!


#32 No Kidnapping Today

Once, when I was about 10, I got in the passenger side of what I thought was my dad’s car. I was waiting for a few minutes and then the real owner of the car came. At first, I was terrified that he was going to kidnap me and steal the car, so I started scrambling for the door handle. Then he started yelling at me for being in his car. That’s when I realized I was in the wrong car and booked it back to the store, where my dad was waiting and laughing hysterically. He saw me get in the wrong car and just waited to watch it play out.


#33 The Winds Of Disgust

When I was about 13, I went on a school trip which included a boat ride.

It was a windy day and the sea was rough, so like most of my friends, I got extremely seasick. The toilets were full of puking school kids so when it was my turn to churn I found a space along the rail and let loose.

I aimed down at the sea but the wind whipped my vomit about 20 feet over to a middle-aged man who was enjoying the sea air. As I watched in horror, he registered that he was being spattered with something, but it was only when my second wave hit that our eyes met and I saw his face change from confusion to horror.

I had no words, just more vomit, so he hurried off, presumably to clean himself. Thankfully, I didn't see him again; but I'm sure I ruined his day.


#34 Accidentally Insensitive

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. He said he watched it religiously and was hoping to get selected as a contestant. 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 were two black contestants on the show, so when I saw him the next time, I asked:

"Hey, did you catch Jeopardy last week?"

"No, why?" he responded.

"There were two black guys on it," I explained.

He just stared at me blankly for a few seconds, then walked off. That's when I realized I was talking to a completely different gentleman.


#35 Oh, We're Hugging

I went to a new doctor years ago because the medicine I was taking to help quit an addiction of mine was making me very sick. After meeting with her and having a great conversation about how she also struggled with the same addiction for years, our appointment came to an end.

As I was leaving the room and opened the door, I turned around to thank her for the encouraging words. Her arm was raised up in a "gimme a hug, not a handshake position. I thought, okay sure, and went in for the hug.

As soon as I did, I heard her say, "Oh, okay?" in a puzzled tone and immediately realized she was reaching for the door behind me, not asking for a hug. I aborted the hug which made me look more awkward and raced out of the doctor's office as fast as I could.


#36 Dad's Sizing Method

My dad loves buying clothes for me but he's bad at guessing my size. He'll find a complete stranger that he thinks looks like me and have them try the stuff on. Then he'll take their picture and send it to me. It's super weird and I can't get him to realize how creepy it is. My favorite pics he's sent is a five-year-old wearing a hat (we had the same hair color) and a scared looking older woman wearing a coat (we were the same height).


#37 Mistaken Motions

I thought some random guy was trying to give me a fist bump while walking down the street. It turned out, he just was trying to scratch his nose. I just got an awkward high five and fist bump thing. I avoided all eye contact after that and slowly shuffled back to my grandmother.


#38 Not A Player

I played this game with some buddies in college where we would slap each other’s necks really hard. I saw my friend studying at the library, went from behind him and slapped him really hard. It turned out to be some total stranger and not my friend! I almost went #2 in my pants and so did the other guy.


#39 Determined Evangelist

One time, I was driving around town with my friend when I noticed I was being followed by an older car. I made several left turns that eventually made us go in a big circle, to which he followed. At this point, I was getting nervous, so I pulled into a convenience store and turned around. He did the same exact thing.

After this, I decided I’d pull into the closest business and go inside. I pulled into a shop where I knew the owner and walked in with my friend. The stranger followed us in, looked around a bit and said, “My soul is saved... Is yours?”

At that point, my friend, the owner and I were all speechless. The stranger then stared at us, calmly walked back to his car and drove away. I’ve never been so confused in my life.


#40 No Full Service

I worked at a hotel front desk. An old, maybe 75-year-old lady called the front desk and wanted a pillow delivered to her room. When I got there with the pillow, she wanted me to come inside. I’m like "Uh no, here is your pillow," but she insisted, so I did.

I got inside and she shut the door. She told me to put the pillow on the bed, then went to a drawer in her dresser. At this time I was like, “I need to return to the front desk," thinking the worst.

She proceeded to pull out a box of bandaids and wanted me to put them on the open sores on her feet... I noped out of there as fast as I could and left before she came down for morning breakfast.


#41 You're Not Alone

I was standing behind this guy waiting for the elevator in a hotel. We were down in the lobby and it was busy with lots of people coming and going, so he obviously hadn't noticed me. Once the elevator doors opened, he got in, but he still didn't see me walk past him on the other side. As SOON as the doors closed, while obviously still under the impression that he was alone, he let out this heinous flatulence that went on for about ten seconds.

Midway through, out of the corner of his eye, he spotted me standing just behind him. The poor guy almost jumped out of his skin. He was staring at me as if he'd just seen a ghost. I was staring at him with what I can only assume was a fairly horrified expression.


#42 Virgin Toes

The first time I went to get a pedicure, I went with my mother-in-law. She's a very loud woman who often doesn't understand what she's saying. She kept screaming at the pedicurist, "BE GENTLE WITH HER, SHE'S A TOE VIRGIN. SHE'S A TOE VIRGIN. DON'T POUND HER."

God help me, I will never go back.


#43 Heartbreaking Nickname

An old man behind me in a Walmart checkout called out a common nickname of mine. I turned to face him and didn’t immediately recognize him. He was gushing with tears in his eyes about how much he loved me and how he couldn’t wait to go home with me.

I asked him if it was possible he had me confused with a different person. The guy’s tears started falling, and he began choking apologies through sobs. Apparently, I was a dead ringer for his long-dead wife. Combine that and the dementia setting in and presto, Walmart meltdown.


#44 Beard Molesting

I did something awkward at work. There was a guy who came in with his kids and had a big bushy beard. He came up to the cash register and asked me where to find an item. I was a little overenthusiastic I suppose because I stuck my fingers out straight ahead to point him in the right direction and they went straight into his beard! I felt like I had assaulted him, but luckily we laughed it off.


#45 Where Did You Get This?

One time, I was in a sporting goods store at the mall. Out of the corner of my eye, I saw a shirt with a really cool design and fabric. I started feeling the fabric to see how warm it would be, when all of a sudden I heard, "Dude. What're you doing." I looked up and it wasn't a mannequin. It was a man. My eyes grew wide and I fled. Left the mall even.


#46 Nice Boots

I got on an elevator with a woman and she had on these really nice boots on, so I complimented them by saying, "Nice boots." She cupped her breasts and said, "Well, you're not shy; thank you, they're real." Then I immediately realized I said 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."

Image result for girl wearing bootsUgg

#47 Movie Awkwardness

At a movie theater, I went alone and so was the guy sitting next to me. The couple sitting next to us was having a pretty heavy make out session.

Image result for kissing in movie theatreiStock

#48 Bottle Blunder

I 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 go #1 so badly but I was 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, I didn't think I'd make it. He was still sleeping, so I grabbed a big reusable water bottle and squatted over it. It was blissful relief until I looked over and saw his roommate staring at me in horror.

Image result for girl in guys dormYB Online Access

#49 Making 7/11 Moves

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. He 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.

Image result for 7/11QX 104

#50 Mixed Signals

The first time I hung out with a girl I knew from a bar, I paid for dinner because she had comped me so many cocktails before. She took that as a sign that I wanted to hook up with her and I got really uncomfortable. I ended up apologizing for buying dinner.

Image result for dinner dateDiabetes UK

#51 Donut Joke Gone Wrong

I was at the grocery store with my wife and when we were passing the donut section I said, “I’m going to humiliate those donuts.” I knew it was something that would make her laugh. When I said it, I turned around and saw that there was a woman in line who was not my wife. She didn't laugh.

Related imageWUNC

#52 I Speak Sign Language Too

When I was in college, I was waiting for a shuttle bus and a girl I had previously been in a class with walked up to the stop with a guy I didn't know. I said to her, "Hi, how are you," and we had a short exchange of pleasantries. Then she turned to the guy next to her and in sign language said: " I don't remember her name." So I sign, "That's okay, I don't remember your name either." I then offered my hand to the guy with her and introduced myself.

Image result for sign languageDeaf Access

#53 Uber Misconnection

I took an Uber once where the driver obviously stopped at McDonald's on his way to get me and had the bag on the passenger seat. He kept munching on fries and my desire for them grew so much that I asked him if I could have some. I wish this was a love story and I wish I could tell you we shared his fries and are still great friends to this day, but I cannot. He gave me a firm no and kept on driving.

Image result for mcdonalds seatbeltWhisper

#54 The Things That Go Down In The Stalls

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 going to 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 was watching animated adult videos in the stall next to me made me nervous as all hell.

Image result for bathroom stallsPartitions and Stalls

#55 Be Careful Of What You Say Out Loud

I was at a bar bathroom in a stall doing illicit drugs with a friend and he started talking about the two hot chicks at the bar. All of a sudden, we heard a guy say, "Are you talking about the two girls at the bar?" My friend said, "Yeah, they’re hot." He responded, ‘Well, one’s my sister and the other’s, my girlfriend."

We tiptoed out of there as he was finishing his business in his stall.

Image result for bar washroomDaily Mail

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