People Share The Most Awkward Position Someone Else Has Put Them In


You want to be a helpful person. When a family member, a friend, or even a stranger asks for a simple favor, it’s natural to want to help them out. However, every now and then, a person’s request can go a little over the line. Sometimes, the appeal can even make you uncomfortable and leave you in a totally awkward position. Whether the situation is just mild or downright inappropriate, you’re now involved in the dilemma and are forced to decide how you want to approach it.

Trying to smoothly navigate yourself out of a circumstance you don’t want to be in can end up becoming one of the most memorable (and simultaneously cringe-worthy) moments of your life. Just take it from these people, who recently shared the most awkward position someone else has put them in.

#45 The Crying Teacher

My English teacher took me out in the hall and started crying because I (supposedly) wasn’t being supportive enough of her.



#44 Trained By The Replacement

I was trained to do a job at a company by the guy I was set to replace. I spent an awkward three weeks with the guy and talked with him about the situation. He kept saying he was happy that he would finally be able to go on vacation after he left and that he was thankful the company was hiring me, but deep down he seemed sad about it all.



#43 Fund-Draining Family

My dad told his then-girlfriend that he paid for my student loans and the downpayment of my house. She kept begging him for money so he needed to make it look like he had none. He also figured it would make him look like a good father, in an I-gave-my-daughter-all-my-money-to-help-her kinda way.

I had no idea my father had told her this until she called me screaming about how I was selfish for taking all of my dad’s money. She was like, “He’ll have nothing left for retirement you selfish brat! If you were my daughter I would disown you. Goodbye.” My dad didn’t even defend me or anything. Never said a word.

What bothered me most though was the fact that my dad never, and I mean never, gave me a dime for anything in my entire life. He had to lie to make himself look good but never actually did anything.



#42 Invoice For Parenting

My mom sent me an “invoice” for raising me. I called her to see what was up. She said that if I didn’t pay the amount she would lose the house she was living in. She lamented that I was an expensive child and that I owed her this money. I hadn’t spoken to her four years prior to that. It was a real tough situation.



#41 Awkward Baby Shower

I went to school with a set of twin girls. The first one got pregnant super young. Then, after her baby was born, the other twin got pregnant. At the baby shower for the second twin, the twins’ mom said something about how both of her daughters had learned their lessons and wouldn’t have any more babies for a long time. But during this speech, the first twin’s face changed… Turns out, Twin #1 was pregnant again. The mom ended up yelling at her two pregnant teenage daughters in front of all the guests. Super awkward.


#40 The Facebook Reveal

I was in a school office waiting to be interviewed for an art teaching position seven years ago.

There was another art teacher (who already worked at the school) in the office as well, and she was trying to be friendly and make conversation with me.

She pulled out her cell phone and asked me for my name. A soon as I told her, she immediately logged into Facebook, found my profile (which I left open to “public” at the time) and started reading my profile out loud for everyone in the office to hear.


#39 Texting The Sister

My sister and her boyfriend had 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.

I told my sister about it and they broke up. But after some time they worked out their differences, figured out what was going wrong in their relationship, and got back together. Today they’re doing very well — they have two sons and are engaged. We never talk about that text.


#38 Mumbling For Mormons

I grew up not actively doing any religious stuff despite having lived in an aggressively Mormon neighborhood. On one day when I was in the third grade, I was invited to my friend’s house for dinner, and everyone in his family was a devout Mormon. When I went over, her mother asked me to say grace. Being a stupid 10-year-old with no idea of how to say it, I clasped my hands together and just mumbled under my breath for five minutes. Five minutes. I probably would have gone longer if the mom didn’t stop me.

I didn’t have dinner with them again.


#37 Awkward Paint Night

My husband and I went to a Wine and Paint event one evening. My canvas was angled in a way that made me essentially in view of the couple across from us. There were about six couples at our table, and everyone was pretty quiet as they were focusing on their painting. The woman I was facing randomly asked me, “Do you know my husband?” because she thought I was throwing glances at him across the table. In reality, I was simply looking at the teachers painting behind him. You could feel how uncomfortable everyone at the table was and I wanted to just crawl under the table.


#36 Cornered By The Coworker

I was getting a drink at work and when I turned around a female coworker trapped me in a corner. She demanded to know why I didn’t look at her like the other guys did. She spurted, “I know I’m older than you, but am I not pretty?” I felt so awkward, but luckily another coworker saw us and I just walked away laughing like she just told a joke.


#35 Hesitant With The Homeless Man

When my brother was about 14 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 who was 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!” My brother had to awkwardly stand there with the homeless guy while being pressured by onlookers from both sides, and the homeless guy just stared at my brother waiting for him to decide what he was going to do.


#34 A Tense Thanksgiving

My wife, kids and I were invited to her parents’ house for Thanksgiving, along with her two sisters (we’ll call them Sister #1 and Sister #2). While we were all around the table, Sister #1, out of nowhere, called out Sister #2 for dating her 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 at the table over the age of 10 who dared to speak. It was quite a celebration of love and family.


#33 No Pressure

Meeting my girlfriend’s entire extended family for the first time, which included her autistic brother.

I go around the room greeting everyone. When I get to her brother, I introduce myself and hold out my hand for a shake. As I’m awkwardly standing there with my arm half-extended, he suddenly blurts out: “When will you be marrying my sister?”

The entire room erupts. I turn beet red. The story forever becomes a recurring joke.


#32 Baring It All

My best friend in middle school was a girl who lived near me. One day, I went over to her house to keep her company while her older sister left for a pool party. When it was almost time for her to leave, the older sister came downstairs to the living room wearing what looked like a lingerie set. She was also had a few bathing suits in her hands. She then continued to ask us which of the bathing suits she should wear to the pool party since she couldn’t make up her mind. After choosing one of them, she then proceeded to go fully nude right on the couch in front of us. She was a few years older than us and, I’ve got to admit, she had a really nice body and curves. All she said after changing was, “Sorry guys, I’m gonna be late.”


#31 A Premature Proposition

I had an anonymous admirer who turned out to be my friend’s 16-year-old son. While I was nowhere near his mom’s age, I still had over a decade on him. He insisted we go on a movie date. I refused and never talked to his mom about it because she was a wee bit crazy when it came to her son. I also saw her son as a little brother, so that made the whole situation so much more awkward.


#30 Not Prepared For Pallbearer Duties

When my girlfriend’s aunt died, I accompanied her to the funeral. Despite never really meeting or talking to her aunt, they asked me to be a pallbearer.

It may not seem like it, but to me, it was a really awkward situation…


#29 The Friend Zone Liar

My best friend in high school told me that he had a huge crush on me. I had a boyfriend at the time who I wasn’t looking to break up with, but this guy didn’t care. He tried to convince me to break up with my boyfriend countless times and he couldn’t take the hint that I just wanted to be friends. Long story short, when I finally told him that our friendship was over, he told all our friends that I got intimate with him and now none of them will talk to me anymore. Attempts to explain that he was a lying, deceitful jerk just didn’t work.

The silver lining to it all was that a lot of toxic people were purged out of my life. Later, I ended up leaving with my horrible boyfriend, too. High school was the worst.


#28 Male At The Gyno’s

Male here. One time, I had some blood drawn in a laboratory. I alerted the nurse that I usually fainted whenever I came across needles. In the past, I had already convinced nurses to lay me down on a bed so that they could draw the blood without me fainting.

This time, the nurse was really helpful, but the only place they could lay down was in the gynecology department. Sure enough, I laid down on it, and in the middle of the process of drawing blood, the nurse suggests that I put my legs on the stirrups; you know, the things in that women place their legs on for the gynecology exams. It was sooo awkward.


#27 Covering For The Boss

My supervisor at work was having an affair. He kept telling his wife that he was working overtime but he was actually with his mistress. Anyway, I was working overtime once and his wife kept calling asking to speak to him. I sent him several messages warning him but it wasn’t until much later in the day (and after six or so calls from his wife) that he finally called her back.


#26 Dating Dad’s Stepdaughter

My father has never been in my life. I refused to see him or talk to him. One time, I went out to dinner with this girl I really liked and we ended up making out during our date. When she brought me to her home later that night, I was shocked to find my dad there… Turns out, he was engaged to her mom. Despite the awkward situation, the girl and I decided to still see each other because I knew my dad and her mom wouldn’t last. They broke up two months later.


#25 Inappropriate Dinner Conversation

My mother-in-law is an elderly Thai woman who still speaks broken English after living in America for 50 years. A notable thing about her is that she has a tendency to be… tactless, for lack of a better word. One time I was at a party she was hosting, and without any shame, she asked a guest what it was like being an FDNY paramedic on 9/11 and if he watched people jump out of the towers. After answering very briefly he buried his face in his plate to avoid having to discuss it any further. She then proceeded to ask, “So sweet muffin, how many people you kill in Iraq?” After the dinner, I let her know that she had behaved inappropriately and that a few people’s feelings were hurt by her questions.


#24 Within Earshot Of Discovering Mom’s Infidelity

I was up super late one night (maybe around 4 a.m.) despite the fact that the following day was a school day. I was doing homework, and a couple of feet away from me my dad was browsing Facebook. Suddenly, he started cursing really loud; so loud that the hairs on my body started raising. I asked my dad what was wrong and he said he just found out my mom was cheating on him (he had been going through her Facebook messages). I didn’t know what to do, or how to react, or what to say. I’m terrible at stressful situations, and the anxiety washed over me.

Anyway, the fallout from this was a nightmare.


#23 Breaking News To Parents

My boyfriend and I were looking at apartments to move in together (a first for both of us.) I brought it up casually at dinner with his parents (one of which was more conservative than the other) having assumed that my boyfriend had already told them of our plans. He hadn’t.

Anyway, I started applying for jobs in the same area my boyfriend’s family lived in. He had suggested we move in with them to save money, so I started preparing for that possibility. Once I landed a job, his dad said to me:  “Yeah, but where would you live?” Turns out, my boyfriend, once again, had never informed his parents of our plans… Plans that he had suggested to me.

Great guy, but we aren’t dating anymore.


#22 Visiting The Psych Ward

Someone I had not heard from in three years called to tell me her mom had died. Seeking company, she asked me if I could visit her at the psych ward. Out of kindness and respect, I agreed to visit… But I had no idea that she was on a 72-hour involuntary psych hold for suicide/murder until I got there.


#21 Crying In The Cafeteria

I walked in on a couple breaking up in an empty cafeteria. I crossed about 150 feet on crutches to the vending machines while the guy sobbed. My Cheetos got stuck.


#20 Pulling At Facial Hair

At my new church, I was chatting with two women after the service. One was a lovely, very bubbly middle-aged woman who I ended up becoming great friends with. The other was a slightly older woman; very uptight and with kids my age. While we were talking, the middle-aged woman went up to the older woman and removed a white hair from her face. “Oh you have a puppy hair or something on you,” she says as she pulls it… Turns out it’s attached. As soon as she feels the tug she stops and leaves it on her face. She turns, gives me a quick look, then walks away. She just leaves me. I had no idea what to do or say.  In her defense, it really did look like a pet hair…

To make conversation, I ended up asking the older woman if she liked dogs… It was literally all I could come up with.


#19 Client Inquiry

I ran into a client at a local bar and she asked if my boss and one of my coworkers were married. It struck me as an odd question (because they weren’t) so I asked what made her think that. “Oh, I just see them together around town all the time,” she explained. It then became clear they were sleeping together (I guess I don’t pick up on these things as quickly as I probably should). I then had to sit my boss down and let him know clients were asking. What made it even worse was that he would deny the affair to my face, even though I already knew something was going on.


#18 Breaking Up While Moving In

A friend and I were moving in together and his girlfriend was helping us move. When they took a lunch break the girl decided to break up with him. After lunch, only he came back to finish moving. Super awkward.


#17 Scolding At School

I teach middle school, and one of my student’s parents brought him into my classroom one afternoon to shame him in front of me for his grades in other people’s classes. I guess because I was his favorite teacher, they just wanted me to be there while they chewed him out. Simultaneously flattering and oh so awkward.


#16 Turned Down By A Twin

In my freshman year of high school, my friend (let’s call him Sam) and I had no homecoming dates. We spitballed ideas on who we should ask and decide on asking these two twins that we know. We decided to go to their soccer game to ask them there. Sam’s mom offered to drive us to and from the game.

Fast forward to the day of the game, I got in the car and had just remembered that the girl that Sam wanted to ask already had a boyfriend. I asked him about it, but he dismissed it with, “Don’t worry, it’ll work out, she’ll choose me.” I knew that he had feelings for her for a while, but I didn’t think they were this deep. After the game, I asked my girl to homecoming and she said yes. While we’re all smiles and hugging, I see Sam talking to the other twin. Of course, she said no. He threw the sign and the rose he had made into the garbage and stormed to the car. I sheepishly followed after him.

His mom definitely read the situation during the car ride home. When I got home, the mom peeled away so fast I didn’t even have a chance to say goodbye.

Later in the month, I found out that he had asked out the girl I had asked, despite the fact that I had already told him I had feelings for her. Long story short, no, we’re not friends anymore.


#15 Watching Movies At Work

As an IT specialist, I manage all PC-related items for around 5,000 people and report to the Senior Manager directly. One time I passed by someone’s office and I see the dude inside fully watching an adult video on his work laptop. I didn’t want to rat him out, but part of my job requires reporting on online activities, so eventually, I had to include the incident in my report. While I was submitting the report to my manager, I discreetly discussed the situation. It turns out the dude had been written up before for watching Netflix, so this wasn’t his first offense. That made me feel a bit better, but nothing will erase the horrid memory of what I saw that day.


#14 Unexpected Call With Biological Mother

I was adopted as a kid, but I know my biological parents. I haven’t talked to them since I was maybe three.

I was sitting with my grandmother one day and the phone rings. She was pretty old at the time, so I got to the phone first. I answered the call and brought it to where she was sitting. I assumed it was just one of the many care aides that visited her through the day.

She talked to the person for a minute and then handed the phone back to me. She said my biological mother, who I hadn’t spoken to in nearly three decades, wanted to speak to me.

Needless to say, neither of us had much to say to each other…


#13 Driving By The Cat-Fishers

One of my buddies wanted to go on a date with a “super fine girl” from Tinder, but she had a requirement. Her roommate needed a date, and if he could find her one she promised him that they could go back to her place early to get intimate (if you know what I mean).

So he came up with this convoluted plan where I would drive all four of us somewhere and after hanging out for some time he would say he needed to go back to “study.” Tinder girl would then follow him, saying that she also needed to leave because her phone was dying. For convenience, they would Uber back together… For convenience.

I’m in full-out belly laughter at this point, but I want to see this train wreck. So I agree to go through with his plan.

While we’re driving on our way to pick up the girls, and he grabs my shoulder and says, “Don’t slow down, and keep driving.” I’m slightly worried that there’s a cop or something.

But once we get to the end of the block, I discover that the two girls who were there waiting were completely different from their Tinder pictures. We had just been catfished. So I had to awkwardly drive my friend home while listening to him call this girl and her friend.


#12 A Traumatic Massage

While I was getting a massage, the massage therapist was telling me about her terrible teen years, including the time when she had a stillbirth at home and her parents buried it in the yard. I was 18 years old at the time.


#11 A Language Mishap

My mom has this weird idea that no one else in England speaks French. She tends to talk trash about strangers since she thinks they won’t understand. And it’s true, most of the time they don’t; but one time in the subway she started mugging off this guy with a handlebar mustache who was sitting on the other side of me, next to his friend. I hissed at her in French to stop because what she was saying was making me feel uncomfortable. She laughed out loud, assuring me that English people only know “half a language.” Then handlebar guy started talking really loudly to his friend in French.


#10 Should’ve Been You

I was at my high school friend’s wedding. She and I were close, but we never dated. After the ceremony, while I was dancing with my fiancé, the mother of the bride comes over to me crying, pulls me aside, and says, “It should have been you.” Awkward.


#9 Single Parent Woes

I was meeting with the chair of my department in college to fix a giant problem with my classes. I said something about my mom being a single parent and how that made things tough to balance. He heard me wrong and thought I said I was a single parent, and proceeded to give me resources to help take care of my kids. By the time I realized, it was too late to say anything… He was just being so nice about it. It was the most uncomfortable 15 minutes.


#8 The Thief Friend

One of my (former) close friends got me hired at the store she managed. Not only did she train me incorrectly, and she also stole money from my register. Then she blamed it on me and expected me to pay it back.


#7 An Unwanted Tattoo

I was working at a hospital ER as a paramedic and was starting an IV on this old lady who had a thick Eastern European accent. As I was finishing up, she made a comment about my tattoos on my arms and said something about her own. Of course, being friendly, I asked what tattoo she had. She looked me in the eyes and said, “Well it was something I didn’t want to get.” Eventually, I start connecting the dots — she was just about the right age to have been held in a concentration camp. It got really cold in that room all of a sudden. I had no idea what to say.


#6 Awful Plane Ride

I had to sit next to my friends making out with each other on an airplane while the band director who was one seat in front of us was vomiting and the girl next to us was having a panic attack.


#5 Confessing To The Babysitter

As a teenager, I babysat for a really nice young couple. One day, the wife confided in me that she had been unfaithful to her husband. I think she was just compelled to confess to someone, but I saw instant regret on her face. I could see her thinking, “What am I doing telling a teenager in a small town?!” I was horrified as well. I kept her secret.


#4 Guest Seat Guesswork

I was an usher at my cousin’s wedding and at the reception I had to send everyone to their seats… Except there was no seating chart so I had to pick seats for everyone…

Except I was from out of town and had no clue who anyone was, or who they knew. So how was I supposed to know where to put anyone?


#3 A Sobbing Server

I experienced terrible service at a local bar. It waited an hour for somebody to come to the table, and another 30 minutes for the drinks to get there. The server then came to the table and started crying and complaining about the establishment. She was clearly tipsy and made everybody feel uncomfortable.


#2 The Boss’ Burial

I had to return something to an employer. When I got there, he and three of his family members were burying his dog, who’d just been run over. The mom blamed herself for it and got really drunk, then insistently hit on me, making the employer feel extremely uncomfortable.


#1 Snowed In

My boyfriend of three months and I decided to get snowed in together during a snowstorm that granted us a long weekend off. The snow started to fall, and then a few minutes later someone comes barging into his house. It’s his girlfriend of five years. The snow gets worse and no one can leave for over 24 hours.