Just picture this: everyday folks going about their business, and then, bam! Life throws them into situations that make for epic storytelling at family get-togethers or over late-night chats with buddies. And mind you, we’re not talking about made-up stuff; these are the stories that you couldn’t even dream of. You’ll get the real scoop from the people who found themselves knee-deep in some seriously unexpected and laugh-out-loud awkward moments. Get ready to be both entertained and amazed!
Ended up going to a gas station and filled up my car while this older guy was there doing the same.
We both drove off and ended up at a Starbucks about 2 miles away.
We then both ended up at the gym and ran a few treadmills apart.
We both knew. It was awkward.
I work in a restaurant, and I was going to greet a customer walking in. Right before he came in, my friend Diane was joking around with me and as he walked in I said very loudly ” I Love You” in the tone that you would say “How Are You?”…. it got dead silent, and he looked at me and just said “….I’m going to sit at the bar..” He proceeded to mean mug me all day.
He was lucky to have my love, if only for a moment.
I was riding my motorcycle a month ago when the light ahead of me turned red. So I slowed down and stopped behind the car that was also waiting at the red light. A guy in sweatpants jogs out between me and the car, and for some reason, a TV remote flies out of his pocket and smashes like it was made of glass, all over the street. The sheer randomness of a guy having a TV remote in his pocket made me burst out laughing, and the guy was staring at the shards of the remote in the street like he didn’t know how it got in his pocket. I’m laughing so hard that I ease off my clutch a bit, and scare myself by moving forward an inch, causing me to stall my motorcycle out. I can’t stop laughing, and now my motorcycle engine isn’t covering the sound. So the guy slowly looks up from the shattered remote and stares directly at me with this pained look on his face. He did this until I stopped laughing, fired my bike back up, and drove around him and down the street.
Without thinking, I once tried to shake an amputee’s hand. He stuck out his arm in a non-offended way to show that he was unable to shake my hand, and to diffuse the situation with only minimal amounts of awkwardness. I, for some reason, took this as a gesture to shake his handless arm (it was cut off at just above the elbow so I had to really reach for it) which resulted in uneasy laughs and goodbyes.
Twice in my life, I’ve been in a situation like this.
Once I was walking home from the subway in high school, it was late, and every turn I took this guy in a hoody behind me took the same turns, like 3 times in a row. It was late. I started to get extremely scared. When I got to my street, I walked till I was just around the corner and then took off sprinting thinking he would be after me. After half a block I looked back and he’d just kept going, not changing pace at all and he wasn’t even looking at me.
The second time, I was walking somewhere in NYC, and it turns out I was going to the same bar as this girl who was about 15-20 feet in front of me, so I “followed” her for like 34 turns and ended up behind her in line at the bar… awkward as h*ll.
I was at a wedding reception at a golf course once and thought the entire patio was filled with wedding guests. Drunk and hungry, I also thought all the food at the tables were wedding appetizers. Turns out there were regular country club members on the patio as well. Feeling social, I sat at one of the tables and started eating part of their shrimp cocktail appetizer and chatting them up. Unfortunately, they weren’t part of the wedding, and I was stealing their food. I probably sat there for 10 minutes until I came to the horrible realization of what was happening.
After taking a very stressful French exam during college, I went to the bathroom. All the stress from my life just kind of hit me at once, and I started bawling. Several minutes into my nervous breakdown, some dude walks in to find me sitting in the corner near a sink just sobbing. He was so uncomfortable, and I could tell. It was so ridiculous that I started laughing uncontrollably like crazy… the dude just turned around and left.
I ordered pizza online from Dominos and tracked it as it was being made. (If you haven’t ordered online before, it tells you by name who is preparing your pizza, etc).
Anyway, it told me Diego was on his way to deliver the pizza, so when the delivery man buzzed I opened the door and said a very friendly, “HELLO DIEGO! Thanks for delivering my pizza!!!”
The man (who happened to be of Latin descent) just stood there and looked at me for a minute. Then said, “My name is Luiz.”
…I could have tried to explain, but I was really hungry. So I paid the man and ate my pizza.
When I was 13, I was at the local convenience store with friends in the middle of winter. We all decided to get some frothy cappuccinos to warm our spirits. I decided on the French Vanilla, while my other friend went for an English Toffee. We paid while our other friends were perusing other items and started walking towards the door, with me walking in front. As I approached the door, I took the cap off my frothy beverage, smelled it, and turned back to my friend with my eyes closed while giving an over-the-top and obnoxious “Mmmmmmmm” sound.
When I opened my eyes, I realized it wasn’t my friend but an extremely unimpressed middle-aged woman with glasses. We stared at each other for at least five seconds, me rooted to the spot in shock, and her judging me. She then moved past me and left.
It turns out my one friend doubled back to go talk to the other friends perusing other things, and the middle-aged woman had purchased her things right after mine. My friends saw it all and were dying of laughter.
When I was a kid, I liked to extend my arm fully out of the window to feel the wind. On one occasion I was riding with my dad who lived in the city, and we were driving down a particularly narrow street with two lanes. As usual, I had my arm hanging out of the window, and I ended up SLAPPING an older black gentleman right in the face in the car next to us as we drove by. He immediately started shouting at me, and I began rolling up the window (non-automatic window) as quickly as my little hands would roll.
I was getting onto an international flight, and the flight attendant asked for my passport. I didn’t hear him though, and I just saw him extending his hand out towards me so I reached out and shook his hand. It was at that moment that I realized what he said to me. He just laughed and tried to save us both from a really awkward moment by saying ” Nice to meet you. Do you have your passport?”. I apologized and opened up my bag to look for my passport. I looked behind me, and a line of people had started to form so I tried to hurry. I had a newspaper in my hand so I tucked it under my arm. As I started opening up all of the pockets in my backpack trying to find my passport, I dropped my newspaper. I went to pick up the newspaper and as I bent over the contents of my backpack fell onto the floor. I felt so awkward that I was apologizing to other people for subjecting them to my awkwardness. I found my passport, showed the flight attendant, and proceeded to gather up my things. At the end of the flight though the flight attendant shook my hand so I think we’re cool.
I farted while I was in line for Black Friday. Sounds normal, but this was not just a fart. It was the most putrid fart I have ever laid. The lady behind me then yells ” Holy sh*t. Did you fart? Holy sh*t that smells terrible.” So Awkward.
I was once in one of those human-sized mazes. It was a pretty big one, and I was probably 25 minutes into it when I started to have the urge to pee. I snuffed it off and just thought I would go when I go out. Fast forward another 20 minutes and I had to pee so incredibly bad. I was frantically power-walking my way through this maze to find the exit. I was interrogating strangers on how to get out, but I was getting nowhere. I now find myself running through the maze, trampling over children as I quickly round blind corners. being a complete a**hole. Finally, a part of the maze I haven’t been to yet! I thought this must be it! I am home free! MOTHER F*CKING DEAD END. I froze. I stood there, alone, scared, and helpless. I had to urinate so badly that I literally could not move a muscle. I tried to take a slow step forward, and it was let loose like a gushing fire hydrant. I was so defeated during the moment that I didn’t even think about pulling my pants down and just going all over the wall. Pee had won. It got what it wanted. There I was having to accept all this like I had just lost my dog.
After I soaked my pants, I slowly turned around and started to walk out. I could hear some girls coming around the corner and knew I was in for it. Of course, it was some pretty girls that looked at me like I was a freak. And I just said to them like it was no big deal, “Yup, peed my pants.” They didn’t say a word to me. It took me another ten agonizing minutes to find my way out of the maze. Everyone laughing, pointing, and making faces at me. It was horrible. I couldn’t escape it, literally.
Even when I made it out one of the employees asked what happened and I just gave him a cold stare. My face read, what the f*ck do you think happened.
I was trying on some pants in the changing room of some store. I had closed the curtain, but it didn’t go all the way down to the floor. Like I usually do in those situations, I put my shoes under the curtain to make sure that everyone sees that it’s occupied.
I take off my pants and as I’m about to try on the new pants, some little kid opens the curtain and I’m literally caught with my pants down. We make eye contact for a good three seconds before I tell him that it’s occupied and that he should GTFO. He walked away laughing, and I still wound up buying the pants.
So sometimes at work, customers shake my hand as I’m done with their job. As a mechanic, I’m always dirty as sh*t, part of the job. If my hands are particularly dirty, I usually opt for a fist bump. An older gentleman went to shake my hand, and he didn’t understand a fist bump. I ended up teaching him how to fist bump, and immediately afterward he giggled and said he felt like a hooligan. Was weird but hilarious.
Once I was dragged along to a clothing store with my girlfriend, and as she shopped, I decided to try and pass the time and go on my phone and check out what was going on on Reddit. As it turns out, as I was lost in Reddit land, my girlfriend decided to take a sharp turn down an aisle, which I didn’t see at the time. Out of my peripheral vision (I was looking down at my phone the whole time) I saw what I thought was my girlfriend (same-length blonde hair, etc.) and continued to follow “her” around. As it turns out, my girlfriend was off shopping in some completely different part of the store, and I was following a random girl around (at a pretty close proximity) for about 3 minutes. I found out it wasn’t my girlfriend when I decided to act mildly interested in what she was looking at, and that’s when I said “That would look nice on you” before realizing, to my horror, that I just followed a complete stranger around a store for 3 minutes before stopping at a display table with her and telling her to buy a shirt. Her reaction? She looked at me, smiled nervously, and then booked it away from me, while I stood there.
That dance that usually ends up happening when you walking towards a person and don’t know whether to go right or left.
The worst of which was when the dance ended with the both of us crashing into each other …but then we looked at each other acknowledged our stupidity and moved on.
My wife and I were walking home from a movie one night, when a homeless man, who we see all the time, was holding out a cup soliciting donations.
“Spare change?” he said, holding the cup in my direction.
“No, thanks,” I replied.
I took a couple more steps and realized that I sounded like a complete a**hat by answering his question as though he were offering me change.
I stopped and went back, and awkwardly tried to explain that I’m not a jerk, and I didn’t mean to sound like a total DB. He laughed and said he’d heard it a few times before. I gave him a few dollars, and we went on our way.
I had a job as a server a few years ago. I had a married couple seated in my section one evening that seemed normal when I first approached them but as the night continued their conversation grew more heated. I was eavesdropping on the conversation when I visited the table, and they were clearly in the middle of some serious domesticuffs. In the end, the man had asked for a divorce and stormed out as I was approaching the table with their appetizers. I kind of just stood there like an idiot while she sobbed in front of me asking for the bill.
This poor girl walked into my lecture by mistake about halfway through. This particular professor really enjoyed talking to all of his students and was super engaging, even with 400+ students in his class.
When the girl walked in, my professor stopped teaching, looked at the girl, and asked if she was in the class. She said she was and began walking towards the front where the open seats were. This is a fairly large lecture hall, and all 200 students (approximately how many actually show up to class) were now forced to watch this poor girl walk towards a seat because the professor didn’t continue talking and just stared at her.
She got close to the front, and I think the pressure of the whole room got to her and she said, “Actually no I’m not,” and turned around, and we all had to watch this poor girl climb back up the stairs and out of the hall.
I was literally watching my worst nightmare.
I was at a funeral for one of my husband’s relatives. On my way in, an employee of the funeral home asked me when I was due. I wasn’t pregnant, but I am fat and was wearing an empire waistcoat so I wasn’t offended. As I signed the guestbook, I corrected her and tried to defuse the situation with a joke about burning that coat later.
But she just. wouldn’t. stop. She kept trying to apologize and explain herself, and I just wanted to run away. Then I was stuck in a small room with her for the next 2 hours.
I was interviewing for a big promotion at my old job. I had put in the time, the hours, and the effort for this promotion, and I had been passed up a few times, so I was sending out resumes while trying to get this promotion. I went through the first interview, and everything seemed great. They invited me for the second interview. I was so excited.
Flash forward two days, and I go in for the interview. The interview is with the Regional and site managers. Everything is going great. They are asking me “What are your priorities, goals, etc” At the end, the site manager changes his posture and says, “Would you say that you’re a loyal employee, nessabessa34?” Taken aback, I say, of course, I’ve been here almost 2 years, etcetera. And like a shark circling his prey, this dude turns his computer monitor around and shows me my PRIVATE Facebook posts that I posted that I was in the market for a job in the same field.
Now, there’s no way he could have seen this, as it was a friends-only post. Someone I work with had to have tattled on me here.
He then proceeded to read them to me out loud, not only the posts about my job search but also personal posts about my health situation and questions that I didn’t bring up to anybody other than personal friends. I look at the regional manager, and this guy won’t look me in the eyes. He is shifting, obviously uncomfortable.
I tried to say that I was looking just in case this promotion didn’t work out, as I am a college student paying my way through school, but he kept interrupting me and saying “Loyalty is key”
He then tells me “We will think about it” And points toward the door. The regional manager kind of coughs and goes to shake my hand, but by that point, I was already out the door. So I said “Thanks anyways” And then proceeded to have the most uncomfortable walk back to my desk, (I was wearing heels for the first time in like a year so I stumbled on my way out the door) with coworkers asking for the details if I got the promotion.
Not as uncomfortable as some of you, but this one was definitely a top for me.
Oh sh*t. Reading the comments, I remember my by far worst moment. I was at my aunt’s house for Christmas meetup (my whole family from my mother’s side is always there) and we were just talking about some stuff. The “sh*tty life pro tips” subreddit came into my mind, and I told her that there are some tips like “you should drive faster when you are drunk because driving drunk is dangerous and you get home faster”. I was laughing. She just sat there, looking at me like frozen, and then told me with her voice breaking: “That would be funny, but did you know that one of my best friends died 2 months ago because he was driving drunk? And he was too fast.” She then started to cry. I really wanted to stop existing at that moment, trust me.
When I was 13 or 14, the guy I had a crush on took me to a park to talk and learn to know each other. We sat under some trees, and everything was going pretty well, until guess a bird shat on my head while I was talking to him. I had to go back home to wash my hair a few times.
I was at a wedding and ran into my ex gf (dated for a couple of years) and her husband. I am on good terms with both of them. The guy is a super nice dude, and my ex is an amazing person. And everyone was a little drunk, and her husband kept saying weird sh*t to me like:
“Hey man, thanks for giving me a chance with your girl”
“I’m glad that you gave her to me”
“Me and her wouldn’t have been possible without you”
and he just kept going on and on. Which btw, I had nothing to do with the two of them being together. She and I dated for a while, broke up, and moved on. So, this whole thing was all completely random. And the whole time I’m looking at the girl and she is looking at me like.. okay dude please shut up now lol
I have a regular breakfast place that I have been frequenting on the weekends for about a good 5-6 years. One day I went to work later because of a doctor’s appointment, so I decided to pick up some breakfast at my regular place. I walk in, and I take a look around to find a spot to sit at, and I see my dad. He’s sitting in a corner spot with some woman I don’t recognize. He looked shocked, and I decided to walk over. He stands up and gives me a kiss/hug and introduces her as a coworker. It was the most awkward introduction of my life. My dad was an AC Repairman and was strictly on the road. No women in his office. I pretended like I believed him, said hello, and sat down on my own.
Definitely one of the most awkward moments of my life that will stand out for a long time.
More background: My mom and dad haven’t been together since before I was born however he was married to another woman when this took place.
The waitresses were all my friends, and a couple of days later when I went for breakfast, they proceeded to tell me how he met that lady there every week.
I never brought it up to him and pretended it never happened. That was about 14 years ago… I still go to that breakfast place and the girls told me after that day he never came back to that restaurant.
In a couple of weeks, it will be 1 year since he passed. I’m glad I got this opportunity to think and talk about him.
When I went on my first solo date back in high school. I had a huge crush on this girl. Thought she was really cool and I loved her art, and I couldn’t believe she said yes. We went to the zoo because it was free and we were just broke teenagers and we had a blast. Went to grab some food at this place before having to split off to go home.
Our trains were heading in opposite directions, and the entrances were across the street from each other, so I walked with her to her side to say goodbye. I closed my eyes and awkwardly leaned in to give her a kiss goodbye, and she went in more for a hug. I ended up headbutting her in the face, and her nose started bleeding. I was so embarrassed and didn’t know what to say, so I just asked, “Are you okay?” She replied, “I think so.” Still not knowing what to do I just said, “Okay, bye!” and then ran across the street to catch my train.
It was so painfully awkward and embarrassing, I avoided her for weeks after that
I was once traveling through Europe with a group of around 10 folks. We stopped in Paris one night and went out, we had a lovely dinner, and then everyone was sticking about for drinks after.
There was an old man who was sitting alone at the table next to us. One of my friends asked him if he wanted to sit with us and he seemed quite happy about that. a few hours on the man told this whole story about how his wife had passed away last year, she was the love of his life and they had planned to go traveling together, but her illness took her before they could go, and he was now traveling around because it was one of the last things she had said to him. He goes around to all the places that they had said they would visit together and he buys postcards to bring home and put in a wee area with photos of his wife back home.
Now this guy was pretty much speaking uninterrupted. We were just listening to this beautiful story. Everyone was a little bit drunk, but out of nowhere, after he had finished his story, told us all about his wife, and shed a few tears. one of my friends absolutely blitzed. After a moment of silence, goes:
“So! What’s a good-looking man like yourself doing all on your own?!”
the old guy kind of looks at us and says “Well, if I could be with my wife I would be. “The friend replies with “Ah c’mon you gotta get out there you know? You should go talk to her” pointing at a waitress.
We were horrified and were just like ‘nooo stop talking’ because he had somehow completely blanked out this whole conversation with this guy.
and I get up and start to get him up to take him back to where we were staying, and he, while moving is just like “you only live once” and keeps saying things like that while we walk away.
The next day he was mortified and had no idea of the encounter and didn’t even remember meeting the guy.
I’ve told this story once before, but when I was around 10 years old, I was sleeping over at my best friend Juan’s house. We usually stayed up really late playing and would sleep in until like 11 or 12, which I loved because I rarely got to do that at my house.
At about 8 am his dad came into the room and told me to get dressed because he needed my help. His dad was a big drinker, so either his breath reeked of beer from last night or he had one for breakfast. Either way, he was a bit buzzed. He told me he needed my help picking out a toy for Juan as a surprise and we were going to drive to Walmart.
So we got in the car and drove down to the Wal-Mart which was like 10 minutes away from his house. It was a pretty awkward ride, and he started asking me questions to make small talk, like how I was like school and if I had a girlfriend yet.
We get to the Walmart, and he takes me to the you section and asks me what toy I think Juan would like. I walk around and see Darth Vader’s Tie Fighter. Juan and I were huge Star Wars fans and even went to go see Empire Strikes Back in theaters when it was re-released, so I knew he would like it. He buys the toy, and then we have another awkward car ride back.
He thanked me for helping and asked me to keep it a secret. I changed into my pajamas again and tried to go back to sleep, but about 10 minutes later his dad came in and surprised him with the toy and gave me a wink.
I found out a few years later that the reason he had me go on this mission to get the toy was because he had been really drunk a couple of nights ago and hit Juan and he wanted to make it up to him. As far as I know, that was the only time that ever happened, but I don’t really know since we lost touch after 8th grade. It was just such a strange and awkward morning.
Maybe not the most awkward moment but it is up there. I was going on a date with a girl from Tinder, but she didn’t really show her face much in the photos, but I thought, hey she’s pretty cool. I’ll meet up with her and see what she’s like. The only thing I could see from the photos is that she’s Chinese (she also told me this later). So I got to the bar early and sat around, and she texted that she was almost there. Then, as I was on my phone, an Asian girl walked up and said, ‘’Hey!’ So I kissed her on the cheek and hugged her and said, ‘’Hey! How are you?’ And tell her it’s nice to see her.
Then she pauses, looks at me confused, and says “Can I get you a drink or anything from the menu?’
….
Turns out I kissed and hugged the waitress thinking it was my date, and I just froze. ‘I’m so sorry. Oh my god, are you not my date?’ And she goes ‘Uh no…’ and we proceed to start laughing. I ask her to get me a double shot of gin while I get all red-faced. She was actually a really good sport about it. Later my date showed up, I told her what happened, and we laughed it off. Won’t be going back to that bar.
Was on a lounge patio with some friends for some beers. We frequent this place so we know a lot of the servers. Most are around our age, and one of my friends used to work at this place. Anyways, our server is making small talk with us and sees this man in his 50s walking into the restaurant/bar from the parking lot. She instant starts ripping on him to us about how creepy this guy is and how he’s always hitting on her and the other servers. We have a small laugh about it, and she heads back inside. Well, this guy makes his way onto the patio and sits down with a woman at the table next to us who was definitely in earshot the whole time and definitely heard her ripping into this guy who I assume was either a date or a husband. We left and always wondered how she dug herself out of serving them.
Work at a bank and do notaries for people who walk in. Had a young couple come in for a notary, maybe mid-20s. We sit down, and I ask “So what are we notarizing today?”
“Divorce papers.”
Well, so much for small talk.
So they take out their IDs so I can jot down their info. His ID was a little older and had a picture from when he was a lot younger. She looks at it and comments “That’s not the same person”.
I don’t think much of it as I continue to write. Then she says:
“That person was nice”.
I’ve never been so uncomfortable in my life. Finished up and got them the h*ll out of there ASAP.
Whenever I shake someone’s hand I wait until they start to let go(idk why I do this, but it’s something I do),I met someone from my dad’s side of the family for the first time, and turns out they do the same thing so we ended up shaking hands for about 1 minute.
I still cringe about it 2 years later…
I was in a public bathroom with one of my friends peeing two urinals apart (as all men should), when some guy walks up to the urinal between us, drops his pants around his ankles, lets out a huge fart, then pulls his pants up and walks out of the bathroom. My friend and I were in shock, then burst out laughing for like 20 minutes. To this day, the funniest sh*t I’ve ever seen.
I had a blind date take me out and introduce me to is WHOLE family on the first date. I’m talking about everyone from great Aunt Lucy to second cousin baby Rick…
I met this guy through a coworker. She said she had a great guy she’d like to give my number to. I said sure. He and I talked a few hours before we decided to plan a date. When I said “Hey let’s meet at this local coffee shop,” he said, “WAIT I have a better idea, a surprise.” I was a little hesitant because you don’t go on a surprise date with a blind date and not end up in the headline news “body of the missing woman found…” but I trusted my coworker of 4 years so I said “sure”.
Well, he organized at a local park a family reunion and introduced me as his girlfriend to EVERYONE there. A woman who he didn’t even really know what looked like or habits or anything to everyone. It was so awkward for me and so embarrassing. I truly didn’t know how to handle the situation post that so I shook his hand said thank you for the lovely time and went inside, I could tell he was disappointed but oh well.
Once I was in a school play 7 or 8 at the time. I had forty lines and had the third most lines in the play. I had studied for hours to get my words right and then when I got on the stage. I cried. Never lived that down. Some people still remember me as the kid who cried on stage
I work for a cable/internet service, and I had an install at an apartment that is known for temporary housing, where the apartment is completely furnished. They give us the key to go in and do the installation and when all is done stop back to the office and return the key. Well, I was given the wrong key and ended up in the wrong apartment. I unlock the door and enter. As I’m looking around I’m thinking ok they must have already moved in. There are open soda cans, beer cans, pizza boxes, etc. I get to the entertainment center and already see equipment installed. I check my work order, and as I realize I’m in the wrong apartment, I hear the door starting to unlock, and here enters a young lady. Before she had the door open, I announced I was from the cable company, and she was like, what the h*ll? How did you get in? I think I was more fearful than she was. As I’m explaining, I got the key from the office. My voice is shaky I’m shaky, and she’s more p*ssed that the office gave me the wrong key. I apologized and gave her my supervisor’s number and called him to explain. She stated she wasn’t going to call him but ended up doing so. Now anytime I have an install at those apartments I also have a leasing agent with me during the duration.
My cat had recently died, and my family was looking to get a new one. A woman in the newspaper had an ad for a litter of kittens. My whole family trekked out to her place to go look at the cats. We went inside, and we were telling her our story and afterward the lady like reached over me. Nervous wreck and socially awkward 7th-grade me totally thought she was going in for a hug when she was really going for the light switch in front of which I happened to be standing. So I went in for a full-on hug. The lady was sweet and returned the hug, but I still remember this moment and cringe.