We’ve all been there. That moment when you're put in a totally uncomfortable position and don't know what to do to get out of it.
We’ve been in the wrong place at the wrong time, forced to deal with the wrong person saying the wrong thing in the wrong way. Whatever possesses people to have such poor judgment in handling their social interactions, one thing is abundantly clear—it’s not fun being the person who has to face the consequences of their poorly timed bad choices. Whether it’s dealing with awkward silence, too much information, or just witnessing someone make a fool of themselves, being part of an awkward encounter sucks to a degree that few other experiences can match.
Here are 42 stories about some of the most uncomfortable, awkward situations people have ever found themselves in.
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42. Out With the Old, In With the New
Being trained to do the job by the guy you are replacing was the worst. Three weeks of hanging with the guy, talking, learning that he thought he was going to be able to go on vacation after I finished training, and how thankful he was for them hiring me.
41. Anyone Could Easily Have Forgotten to Mention That
I’m about to go for supper with my mom's new boyfriend, she's 50. I didn't know my parents were divorced.
40. Well, I Guess That’s One Way to Learn English
My English teacher took me out in the hall and started crying that I wasn’t supportive enough of her. But as awkward as that was, it fit in well with the rest of my school experience.
Sometimes I think my school was a sitcom, one year 20% of the junior class was expelled for drugs, we didn’t have water for a while because someone punched and broke a water fountain, there was a spirit week that was salad dressing themed, and there was a rebellion against a Spanish teacher for four months until he showed us the movie Cars.
39. Keeping up Appearances
My dad told his then-girlfriend that he paid for my student loan and down payment for my house because she kept begging him for money and he needed to make it look like he had none. He also figured it would make him look like a good dad. “Gave my daughter all my money to help her” kinda thing.
The way I found out he told her this was when she called me SCREAMING that I was selfish for taking all of my dad's money. “He'll have nothing left for retirement, you selfish piece of garbage! If you were my daughter, I would DISOWN you. Goodbye!” My dad didn't defend me or anything. Never said a word.
What bothered me most was the fact that in reality, my dad never, and I mean literally never, gave me a dime for anything in my entire life. He was willing to lie to make himself look good but was never ever willing to actually do anything to make himself good.
38. Monkey in the Middle
I was driving, third-wheeling with a buddy and his girlfriend. They broke up after a heavy argument during dinner, before the movie. I had to drive them to their own houses and I dropped the girl off last and got a whole ear full of what my buddy was like to her.
37. Letting the Cats Out of the Bag
My best friend was a womanizer when he wasn't in a relationship. And one night at a bar, he thought it would be fun to just flip a hundred-dollar bill on the bar top and literally run right out the door.
Then three women converged on the bar. And they were looking for him. They knew I was his best buddy, and then a cat fight started.
After the bar closed, I hung out a bit for after hours. The bartender was laughing his head off. I didn't think the situation or the claw marks down my arms were that funny.
John and I had a good long talk the next morning.
36. Call of Duty?
At my on-campus job, the manager was sleeping with an employee. His wife was very suspicious. I often had to answer the phone when she called or she would stop by right after he left with his side piece. I never explicitly said he was having an affair to her—I didn't have absolute proof at the time—but I didn't cover for him in any way at all. I knew he was pissed that I wouldn't lie for him but he knew he couldn't say anything about it to me.
35. Not Exactly a Joyride
This chick asked me to be her boyfriend while her mom was driving me home and we were in the backseat. It was really awkward when I said no....
34. Rumor Has It
Sophomore year of university, some random dude starts talking to me in the student lounge. He's amusing enough, so we converse until I go to class.
After I left, the dude started telling everyone we were going to hang out later and he couldn't wait to take me to bed.
One of the people he told this to was a male (toxic) friend of mine who had major hangups about my not being interested in him romantically.
I had to deal with the fallout of toxic friend's hurt feelings, outrage, and anger because some stupid dude I never saw again decided to lie about me.
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33. Casting for the Performance
I was working for a small tech startup. At the time, our programmers were trying to create a fairly complex automation that would accurately overlay image files on top of other images by finding common points. To build the automation, we created a sample batch where we manually overplayed the images.
Anyway, the owner of the company invited a very wealthy investor (like billionaire wealthy) and his team to check out this new program. The owner had asked me to demo the overlay automation. The only problem was that the program didn’t work, so I would just be demoing the sample batches (which were done manually) while saying the automation did it.
I refused, citing that this was really unethical. They decided to have another manager do the demo. I mean, did they think these people would just throw money at them without doing their due diligence?
32. Doing Some Oppo Research
I was waiting in a school office to be interviewed for an art teaching position in a middle school, about seven years ago.
There was another art teacher who already worked at the school in the office and she was trying to be friendly and make conversation with me.
She pulls out her cellphone and asks me my name. I tell her and she immediately logs into Facebook and finds my profile—which I left open to public at the time—and immediately starts reading my profile out loud for everyone in the office to hear.
31. A High School Romance
My high school English teacher read us erotic poetry she wrote about her husband... who happened to be our History teacher.
30. Called Out at an Awkward Time
Girlfriend's roommate and her boyfriend were a hot mess, it was just constant tension around them, and the rest of the friends, being great people, absolutely had bets of how long it'd last.
So anyway, one night after another incredibly awkward double date of dinner and a movie and then back to their dorm, we start hearing them going at it (fighting) in the next room. Girlfriend put a shirt on, stormed over and started screaming at them something to the extent of "SHUT UP AND TAKE YOUR ARGUMENT OUTSIDE OR SOMETHING, SOME OF US ARE TRYING TO GET LAID."
As many bad memories as I have of that relationship, I will always love that moment of her half-naked screaming at her roommate to take their drama outside.
29. The Living Room Will Never Be the Same
My old roommate offered a dude our couch to sleep on if he paid for the cab home. I got in the cab not knowing about their little deal.
We get home, she then staggers up the stairs, completely drunk. I hear him pacing around downstairs and ask if she had made him a bed or like, what he’s even doing there. She tells me about their deal, and I make her give him a pillow. Whatever. He sleeps. She ends up falling asleep on the couch opposite him.
It’s the morning, and I wake up to her coming into my room to tell me he woke up and immediately whipped his genitalia out and started pleasuring himself in front of her. She tells him it’s fine and just to “not to make a mess on the couch,” despite it not being fine, in her opinion or mine.
She’s obviously uncomfortable, hence why she came into my room to announce what had taken place downstairs. So I was assigned the job of telling the dude to get the heck out of our house and that I don’t generally take kindly to randoms coming over and exposing themselves all over our living room.
She had pulled a bunch of wild stunts in our time living together. And many a time I had to tell people to screw off, including her.
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28. Principles Before Coworkers’ Feelings
Had a coworker tell her husband she was going for girl’s nights with me when she was cheating on her husband. She wanted me to play along if he called and I said no.
27. The Odd Man Out
I got asked to a Sadie Hawkins dance by a girl I didn't really know, but she was going with a group of some football buddies I was fairly good friends with, so I decided to say yes. It was four couples and we were the only two not dating.
Lo and behold, we get to photos and every other couple has a spat. Like full-blown, yelling and screaming fight. For around an hour and a half as we walk around downtown at different local photo ops.
And then the same thing happens at dinner. For around another hour and a half.
And at the dance. Which we spend all of 20 minutes at.
They asked me to go bowling after the dance and I opted out. I felt bad, she was a nice girl, but I couldn’t handle that situation anymore.
26. Let’s Hope It Was an Autocorrect Typo
The time my sister and her boyfriend moved back in with our parents and one night he texted me from their bedroom saying that he was starting to have feelings for me.
Since then, they broke up, worked out their differences, figured out what was going wrong in their relationship, and got back together. They are now doing very well, they have two sons and are engaged. We never talk about that text.
25. A Very Graceful Performance
I grew up not actively doing religious stuff and I lived in the middle of an aggressively Mormon neighborhood. One day when I was in the third grade, I was invited to one of my super Mormon friends’ houses for dinner. I went and her mother asked me to say grace. Being a stupid 10-year-old with no idea how to tell them I didn't know how, I clasped my hands together and mumbled under my breath for five minutes. Five. Minutes. I probably would have gone on even longer if the mom didn't stop me.
I didn't have dinner with them again.
24. Her Imagination Was Painting a Very Uncomfortable Picture
My husband and I went to a Wine and Paint event one evening. My canvas was angled so I had to face the couple across us and to the left a little bit. There were about 6 couples at our table and everyone was pretty quiet focusing on their painting. The woman I was facing randomly said, “Do you know my husband?” to me because she thought I was looking at him from across the table. In reality, I was looking at the teacher’s painting past him. You could feel how uncomfortable everyone at the table was and I wanted to just crawl under the table.
23. Taking One for the Team
My coworker lived 40 minutes away from work, I live 15 minutes in the other direction. My manager asked me if I could give the guy a ride home because his car wouldn’t start, in front of him, right after I said my only plans for tonight were the gym. The guy was incredibly nice and I got along with him really well. I didn’t want to make my 15-minute commute into a hour and a half commute and miss my workout. But I wasn’t going to make him call a cab.
22. So Much for Boundaries...
I’m a recovered alcoholic in Alcoholics Anonymous who’s been sober for quite a while now. Since I give a lot of credit to that program for saving my life, I take it very seriously. Therefore, when working with others there are certain boundaries I don’t cross, because the end result will be an inability to be helpful and of service in terms of passing along the message and helping someone else get and stay sober.
I had been helping a young gay guy who, because I saw a lot of myself in him, I put a bit more effort into helping. Unfortunately, he got discharged from the Navy and disappeared for about six months. Then, one day out of the blue he hits me up on Facebook with a friend request. Shortly after that he messages me early one morning asking what I’m doing, I’m getting ready for work. He states that he had a late night doing karaoke and then proceeds to send me explicit videos of himself. At 4:30 in the morning!
21. Getting a Second Opinion
A befriended married couple keeps getting into arguments with each other in front of me. At some point, they will both look at me and tell me how disgusting the other one is and then ask how I feel about it. It's absolutely not funny. Things are told about dirty underwear, how bad the sex is, what's wrong with their partner’s genitals, everything.
20. Don’t Worry, There Are Plenty of Other Stylists in the Sea
I’ve been at a small boutique beauty studio for the past year and a half. It’s just four employees. The owner and I got close, but I realized I’ve been wanting to go out on my own because our policies and client management styles seem to clash a lot. It’s her business after all, and I’m an independent contractor there.
I told her that after much thought it’s time for me to go. She cried, a lot. It’s gotten to the point where her eyes water up whenever the topic comes up. We even thought it’s best I go before the two weeks notice is up because she feels it’s so hard for her emotionally to see me there.
I feel as though I am going through a breakup. Definitely not how I imagined this going. I literally feel like I broke her heart into pieces and as though this was a real relationship I’m getting out of.
19. I Demand Uncomfortable Answers!
Was getting a drink at work and when I turned around, my female coworker trapped me in a corner. She demanded to know why I don’t look at her like the other guys. “I know I’m older than you but am I not pretty?” Luckily, another coworker saw us and I just walked away laughing like she just told a joke.
18. You Can’t Take It Back
My coworker would often try and be clever and say something mean about me to someone else in Spanish. One time she was talking trash right in front of me with someone in Spanish, and I immediately screamed at her. She said, “You could understand that?” Now she kinda follows me around at work and compliments me, but I don’t buy it. She hates that I ignore her but I couldn’t care less. She’s a married girl looking for trouble.
17. Way to Put Me on the Spot
During high school, a girl who was in my group for a class asked me publicly if I hated her boyfriend at the time. The entire class heard and it felt like everyone was staring at me.
16. An Uncomfortable Party You Won’t Soon Forget
When I was in the military, I had just arrived to my first duty station. I was like an E-3, which is a pretty low rank. We were out at the club for a going away party for one of the Sergeants. My whole platoon was there, drinking and having a good time. I saw the Sergeant dirty dancing with some girl. It struck me as odd because I remember that he was married. But okay, dancing is dancing I guess. I went downstairs to order some food.
As I go down and I’m standing in line, I see ALL of the Sergeants’ wives come in giggling and laughing. They had let the boys stay out and have fun and now, well, I guess they came out to party too. They recognized me from the actual going away party—the club was the afterparty I guess. They asked me where their husbands were. My brain kinda froze up and panicked because I knew what was about to transpire. I said, “Uh...upstairs somewhere, I think”. They thanked me and went upstairs. I got my food and stepped outside for a second, making my way towards the other entrance to go up to the tables and eat. I was completely alone.
As I’m approaching the doors, suddenly they swing open and the wives come rushing out. One of them was crying. Yep, you guessed it, she saw her husband dancing with that girl. She proceeded to hand me her wedding band and engagement ring and told me to deliver them to him.
Now, being a brand new member of the platoon and a low ranking Marine who didn’t really know anyone that well, I was like, holy heck, this isn’t real. Before I said anything, the rings were in my hand and the wives were across the parking lot. That walk up the stairs was the longest walk ever.
I get to the club entrance and bam, a freaking gaggle of sergeants all walked out like it was a movie scene. They all looked at me. I said “Uh, sergeant? Your wife told me to give you these...?” He said, “Okay, thanks.” To make matters worse, when I went to hand him the rings, one of them fell to the ground, resulting in an awkward “It’s now both our jobs to pick it up” kind of situation. Then they all walked away.
No kidding.
15. Liar Liar Pants on Fire
Wow, my English teacher always thinks that when someone is laughing, the person is laughing at her. She then proceeds to “confront” them. It’s so awkward to tell your teacher you’re not doing anything when she obviously doesn’t believe you.
14. So What Was Your Answer?
Me and my wife were saving for a down payment to buy a house. A friend's wife just got into being a realtor.
We were just casually saying where we were looking etc. and they assumed we were using them, despite the fact that the town was 45 minutes away and completely unfamiliar to them.
Right after we bought (not using them) the wife of a mutual friend (my best friend's wife specifically) died of cancer. They decided the best time to confront me and ask why I didn't use them was the funeral, and gave a guilt trip about how they needed the money.
Sorry but 1: you didn't know the area. 2: we never asked you 3: it’s the most important financial decision of our lives and not something you work with friends on.
I wanted to scream that at them, but then I would be the jerk at the funeral.
Fast forward three months later, they tell me an address of a place they are thinking of looking at to buy and ask if it was in a good neighborhood. It was in the worst neighborhood, right next to the overpass where everyone smokes crack.
13. Handled Like an Angel
I repeatedly saw the church sexton stealing communion wine from the sacristy supply closet and sometimes drinking heavily on the job.
I didn't want him to lose his employment, but I also knew that I had a responsibility to report it to the pastor before things got worse.
Thankfully, the pastor listened to my request to deal kindly with the problem and decided to pardon the sexton—giving him the help (therapy sessions) he needed to overcome the stealing and getting intoxicated on the job.
12. Uncomfortable if You Do, Uncomfortable if You Don’t
My brother was about 14 at the time, and he rode his bike to a nearby gas station to buy a soda. On his way in, a homeless guy sitting on the curb asked him for some change.
As my brother went to give it to him, a guy parked in the parking lot rolled down his window and said: "Hey kid, don’t give him your money!" Then someone else rolled their window down and yelled "Don't listen to him! He can give him money if he wants to!"
Then my brother had to awkwardly stand there with the homeless guy while being pressured from both sides by the onlookers while the homeless guy just stared at my brother waiting for him to decide what he was going to do.
11. Point of Contention
When I was at college, I was in a group of three best friends—let’s call the other two Pete and Carl. We were super close, all three of us, but Pete and I lived together and Carl lived with other friends.
In our first year, both Pete and Carl had serious-ish girlfriends. Seemed very happy. A couple of years later, they both break up with their respective girlfriends. Then, not very long later, Pete started secretly hooking up with Carl’s ex.
I obviously found out, as we lived together and I saw her around our place, but Carl didn’t know and I had to lie and keep it from him. Super awkward and almost lost Carl because of it. Also, there was a lot of movie-style sneaking around that now looking back is hilarious, but was very stressful at the time.
As an example, Carl came over to hang out and I hadn’t realized Pete and the girl were in his room. So I let Carl in and then I hear them. So I offer Carl a drink, then proceed to purposely spill it on him so he goes to my room and I run and tell Pete to sneak her out while Carl is drying off.
It was a happy ending though, mostly. When it looked like it was getting serious, I convinced Pete to tell Carl, and he did, and Carl gave them his blessing.
Eight years later, and Pete and the girl got married and just had a baby. But Pete and Carl stopped being friends not long after college. They say it’s because they moved away and drifted apart, but I know it’s because of this. I moved away from them both and it’s been nearly a decade and they’re still two of my best friends, so they could have stayed friends if they really wanted to.
10. Uncomfortable Eavesdropping
Brother-in-law decided to extort half a million bucks from my old boss using gossip I heard that I repeated to my wife.
DeviantArt
9. And a Hush Fell Over the Crowd...
My wife and kids and I were invited to her parents' house for Thanksgiving, along with her two sisters. While we were all around the table and the food had been served, sister number one discovered that sister number three was dating number one's ex. An angry, awkward silence ensued. The kids started asking why nobody was talking. Potatoes were passed really hard. Platters were smacked onto the table. Stink eye was amply provided to anyone over 10 who dared to speak. It was quite a celebration of love and family.
8. The Elephant in the Uncomfortable Room
So I’m meeting my girlfriend's entire extended family for the first time, including her autistic brother.
I go around the room meeting everyone and when I get to her brother, I introduce myself and hold out my hand. The first thing he says to me, as I'm awkwardly standing with my arm half-extended is, "When will you be marrying my sister?"
Entire room erupts. I turn beet red. The story forever becomes a recurring joke.
7. So Tell Me About Your Qualifications
A friend got me a job interview for a job I couldn't physically do. So awkward.
And the worst part: I didn't even know it was an interview until we had already talked for about five minutes.
6. How Is This the Kid’s Fault?
Sorry for the essay, but this is too messed up not to explain:
I used to have some trashy long-time family "friends." They have a daughter who is about 10 years younger than me. Anyway, they used to make the kid ask me for stuff or favors that they wanted, rather than ask me themselves. That way when I had to say no, it was an extra guilt-trip.
Example: Parents need a "weekend away" (i.e. they wanted to spend the weekend at a hotel in the city). So, when I was over spending time with the kid (I was sort of like an older cousin to her), her mom looks at her and says in a pissy tone "WELL, ask her!"
So the kid, all embarrassed and shy, unable to make eye contact, comes to me and half mumbles "Can you babysit me this weekend while mom and dad are out of town?"
She was like 8 at the time, I was 18. I was only home from school for one week at Christmas, and I had already made plans with other family. She made the kid ask two other people before giving up. When no one would babysit her, her mom blamed the kid. The mom acted all pissed off and gave the silent treatment to the kid, so when the kid finally worked up the nerve to say "Mommy, what's wrong?" the mom freaked out. I was there for all of this. She told the kid something like, "Mommy's upset because her and Daddy don't get alone time this weekend. That's all," and then when the kid apologized her mom replied with, "Sorry means nothing if you don't show it with your actions. People don't want to babysit you because you're too hyper. You know you're allergic to chocolate (she's 100% not), and yet you still eat it."
I can guarantee nobody thinks that kid is too hyper, rude, misbehaved, or anything like that. She was funny, quiet, and easy to get along with. Everyone would have been glad to take her for the weekend for the sake of spending time with her, but I know people refused on the basis of principle.
I feel so bad for how that kid was raised. She's had it rough. Lots of emotional abuse, her mom yelled at her all the time for nothing. This was just one small example of how the mom would put me in awkward positions. I had to cut her off from my life because she was so toxic.
5. Double Uncomfortable Trouble
I went to school with a set of twin girls. The first one got pregnant super young. Then, after her baby was born, her twin got pregnant. At the baby shower for the second twin, the twins’ Mom is saying something about both of them having learned their lesson and not having any more babies for a long time. She noticed the look on the first twin’s face and started freaking out. Twin one was pregnant again. The mom was standing between the guests and the door yelling at her two pregnant teenage daughters. Super awkward.
4. There Is No Joke Here
My mom sent me an “invoice” for raising me, so I called her to see what was up. She says that if I don’t pay the amount, she’s gonna lose the house she’s living in. She then lamented that I was an expensive child (read: health issues), and expressed her feeling that she was owed this money. I hadn’t spoken to her in four years prior to that. Real tough situation.
3. Fancy Seeing You Here!
I matched with a girl on a dating app recently. She was gorgeous, really nice and funny, and all seemed well. We went on a few dates and finally she invites me back to her apartment to spend the night. She told me her roommate would be gone for most of the night because the roommate’s fiancé was in town visiting and they were going to the city to spend time together.
We spend the night doing fun stuff and eventually go to sleep. I wake up in the middle of the night and need to use the restroom. Walking to the bathroom there is a dude on the couch playing Madden. I introduced myself and find out it’s the roommate’s fiancé. He couldn’t sleep either so he invited me for a quick game of Madden. We are playing a game and then his fiancée comes out in the living room obviously looking for him.
The awkward part? The roommate is my ex that I dated for four years and I just eviscerated her man in Madden. Super awkward to explain to my date why I wasn’t comfortable coming around anymore.
2. Office Romance Gone Wrong, and Super Uncomfortable
Ugh, I had this woman assigned to help get me settled into my new job and she didn’t know that I was actually going to be replacing her until I turned up for my first day. Found out after she was gone that the owner of the company had been sleeping with her for a year and had surprise fired her because she was feeling guilty about the cheating on his fiancée and had asked to call things off.
He was a real winner.
I was surprise fired in the same way because his friend had moved to our city and he wanted to give him my job.
NEVER WORK FOR A RICH KID’S STARTUP.
1. The Definition of Uncomfortable: This Story
A female friend of mine threw a party. I lived close by so I showed up a bit early. Knock on the door and the guy I was regularly flirting and making out with at the time answers the door. Shirtless. He says he took it off because he was "hot." So it’s just the three of us sitting around, making small talk, waiting for more people to show up. She's playfully touching him and lets slip that the two of them saw a movie together last weekend. I was too scared to admit that I was apparently the other woman so I clam up and the party eventually continues as planned. We cried together about a week later.
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