When someone you care about asks for a favor, you want to do what you can to help them. However, sometimes their request can be a little over the top and it can make you feel like you’ve been put in an awkward situation. This list is about people discussing an awkward position another person put them in
#45 The Tearful Teacher
My English teacher took me out in the hall and started crying. She said that I wasn’t being supportive of her.
#44 Being Trained By The Replacement
I was trained to do a job at a company, by the guy I was replacing. I awkwardly spent three weeks with him, and I talked with him about the situation. He said he was happy that he would finally be able to go on vacation after he left, and that he was happy that the company hired me; however, deep down he seemed sad about it all.
#43 Money Drainer
My dad told his then-girlfriend that he paid for my student loans, and that he put the down payment down on my house. He needed to make it look like he was broke, because she kept begging him for money. He also thought it would make him look like a good father, as in a I-gave-my-daughter-all-my-money-to-help-her kind of way.
I didn’t know that my father had told her this, until she called me screaming about how I was selfish for taking all of his money. She said, “He’ll have nothing left for retirement you selfish brat! If you were my daughter I would disown you. Goodbye.” My father never even defended me. The thing that bothered me the most was that my dad never gave me a dime for anything in my entire life. He lied to make himself look good, but he never actually gave me any money.
#42 Parenting Payback
My mom sent me an “invoice” for raising me. I called her to ask about it, and she said that if I didn’t pay the amount on the invoice, she would lose the house she was living in. She said that I was a very expensive child and that I needed to pay her back. The crazy part is that I hadn’t spoken to her four years prior to that.
#41 A Very Awkward Baby Shower
I went to school with a set of twin girls. The first one got pregnant at a very young age. Shortly, after her baby was born, the other twin got pregnant. At the second twins baby shower, the twins’ mom mentioned that both of her daughters had learned their lessons and wouldn’t have any more babies for a quite a long time. However, during the speech the first twin made a face… Turns out, Twin #1 was pregnant again. The mom yelled at her two pregnant teenage daughters in front of all the guests at the party. It was very awkward.
#40 The Facebook Profile Reveal
Seven years ago, I was in a school office waiting to be interviewed for an art teaching position. There was another art teacher who already worked at the school in the office as well, and she was trying to make conversation with me.
She immediately pulled out her cell phone and asked me for my name. Once I told her my name, she immediately logged into Facebook and she found my profile (which I left open to “public” at the time) and she started reading my profile out loud for everyone in the office to hear.
#39 The Secret Text
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 develop feelings for me.
I told my sister about it and they broke up. However, after some time they worked out their differences, figured out the issues in their relationship, and they got back together. Today, they’re doing great— they have two sons and they are engaged. We don’t talk about that text.
#38 Mumbling For Mormons
I grew up not actively doing any religious stuff, despite growing up in a very Mormon neighborhood. One day, when I was in the third grade, my friend invited me over to his house for dinner, and everyone in his family was a devout Mormon. His mother asked me to say grace, and being a dumb 10-year-old with no idea of how to say it; I slapped my hands together and mumbled under my breath for five minutes. That’s right… Five minutes. I more than likely would have gone longer if his mom didn’t stop me. I still haven’t had dinner with them since.
#37 Uncomfortable Paint Night
One evening my husband and I went to a Wine and Paint class. My canvas was at a strange angle where I was in view of the couple across from us. There were about six couples at our table, and for the most part, everyone was quiet, as they were focusing on their painting. The woman that was in my point of view asked me, “Do you know my husband?” She asked, because she thought I was throwing glances at her husband across the table. However, I was actually just looking at the teachers painting behind him. Everyone at the table was extremely uncomfortable, and I wanted to just crawl under the table.
#36 Being Cornered By A Coworker
I was just getting a drink at work and when I turned around, a female coworker trapped me in a corner. She wanted to know why I didn’t look at her the way the other guys did. She said, “I know I’m older than you, but am I not pretty?” I felt extremely uncomfortable, but luckily another coworker walked in and I just walked away laughing like she just told a joke.
#35 Hesitant With A Homeless Man
When my brother was about 14 years old, he rode his bike to a nearby gas station so he could buy a soda. On his way, a homeless man sitting on the curb asked him for some change. As my brother went to give it to him, a guy who was in the parking lot rolled his window down and said, “Hey kid, don’t give him your money!” Then another person rolled down their window and yelled, “Don’t listen to him! He can give him money if he wants to!” My brother stood there awkwardly in front of the homeless guy while being pressured by others, trying to decide if he should give the guy money or not.
#34 A Troubling Thanksgiving
My wife, kids, and I were invited to her parents’ house for Thanksgiving, along with her two sisters. While we were all sitting around the table, Sister #1, out of nowhere, called out Sister #2 for dating her ex. Everyone went silent, even the kids asked why no one was talking. Potatoes were being harshly passed around. Platters were being smacked onto the table. Anyone at the table over the age of 10 who dared to speak, received the stink eye. It was a beautiful holiday celebration.
#33 A Quick Introduction
I was meeting my girlfriend’s entire extended family for the first time, including her autistic brother. I went around the room greeting everyone. When I got to her brother, I introduced myself and held out my hand to shake his. As I was uncomfortably standing there with my arm half-extended, he said: “When will you be marrying my sister?” The story is now a recurring joke
#32 No Shame In Her Changing Game
In middle school, my best friend 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 her sister was about to leave, she came downstairs to the living room wearing what looked like a lingerie set. She also had a few bathing suits in her hands. She asked us which bathing suit she should wear to the party. After choosing one of them, she then proceeded to go fully nude right in front of us. She was only a few years older than us, and I have to admit, she had a really nice body and curves. Once she changed she said, “Sorry guys, I’m gonna be late.”
#31 A Teenage Crush
I had an anonymous admirer who turned out to be my friend’s 16-year-old son. I was much younger than his mom, but I still had over a decade on him. He wanted me to go on a movie date with him, but I refused and never talked to his mom about it- because she was a tad crazy when it came to her son. I also saw her son as a little brother, so that made the entire situation awkward.
#30 An Unplanned Pallbearer
When my girlfriend’s aunt died, I went with her to the funeral. I never met or talked to her aunt, but I was asked to be a pallbearer. It may not seem like it, but to me, it was a very awkward situation…
#29 The No Good Liar
My best friend in high school told me that he had a huge crush on me. At the time, I had a boyfriend who I wasn’t looking to break up with any time soon, but this guy didn’t care. There were multiple times where he tried to convince me to break up with my boyfriend, and he couldn’t take the hint that I just wanted to be friends. Long story short, when I told him that our friendship was over, he went and told all our friends that I got intimate with him. Now, none of my friends will talk to me anymore. I tried to explain that he was a lying, deceitful jerk- but that didn’t work.
On the positive side, I got a lot of toxic people out of my life. Later, I ended up leaving my horrible boyfriend, too. High school was the worst.
#28 Just A Man At The Gynecology’s Office
One time, I had some blood drawn in a laboratory. I told the nurse that I normally faint whenever I come across needles. In the past, I would have already convinced the nurse to lay me down on a bed so that they could draw the blood without me fainting.
This nurse was very helpful, but the only place they could lay me down was in the gynecology department. During the process of drawing blood, the nurse suggested that I put my legs on the stirrups. It was very awkward.
#27 Covering Up A Work Affair
My supervisor at work was having an affair. He would tell his wife that he was working overtime, but he was actually with his mistress. One day, I was working overtime and his wife kept calling asking to speak to him. I sent my supervisor 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 his wife back.
#26 Dating My Dad’s Future Stepdaughter
My father has never been in my life. One day, 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. Come to find out, my dad was engaged to her mom. The girl and I decided to still see each other, even though it was an awkward situation- because I knew my dad and her mom wouldn’t last. They ended their relationship two months later.
#25 Shameless Dinner Questions
My mother-in-law is an elderly Thai woman. Even though she’s lived in America for 50 years, she still speaks broken English. She can be very tactless. One time, I was at a party she was hosting, and without any shame, she asked one of her guests what it was like being an FDNY paramedic on 9/11, and if he watched people jump out of the towers. After he answered very briefly, he buried his face in his plate so he didn’t have to answer anymore questions. She then proceeded to ask, “So sweet muffin, how many people you kill in Iraq?” After the party, I told her that she had behaved very inappropriately, and that she had hurt a few people’s feeling by her questions.
#24 Discovering Mom’s Infidelity
One night, I was up really late, despite the fact that the following day was a school day. I was doing homework, and a couple of feet away from me was my dad was on Facebook. Suddenly, he started cursing very loud; to the point where the hairs on my body started raising. I asked him 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 wasn’t sure what to say, I’m terrible at stressful situations. Anyway, the fallout from this was a complete nightmare.
#23 Hiding Plans
My boyfriend and I were looking at apartments to move in together (a first for both of us.) I casually brought it up at dinner with his parents, which I had assumed that my boyfriend had already told them. Well, he didn’t.
Anyway, I started applying for jobs in the same area my boyfriend’s family lived in, because he had suggested that we move in with them to save money- so I started preparing for that possibility. Once I got a job in that area, his dad said to me: “Yeah, but where would you live?” Come to find out, my boyfriend, once again, had never told his parents about these plans. We are no longer dating.
#22 Just A Casual Visit To The Psych Ward
Someone I had not heard from in three years, called to tell me her mom had died. Wanting company, she asked me if I could visit her at the psych ward. I wanted to be there for her, so I agreed to the visit. However, I had no idea that she was on a 72-hour involuntary psych hold for suicide/murder until I got there.
#21 Crying Alone In A Cafeteria
I walked in on a couple breaking up in an empty cafeteria. I was walking up to the vending machine on crutches, and I was standing extremely close to guy who was sobbing. My Cheetos got stuck… It was an awkward situation.
#20 Not A Puppy Hair
At my new church, I was chatting with two women after the service. One of them was very lovely, who I ended up becoming great friends with. The other one was slightly older; 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 long hair from her face. “Oh you have a puppy hair on you,” she said as she pulled the hair from her face… Turns out it was attached. As soon as she felt the tug of the hair she stopped and left it on her face. After she turned around, she gave me a quick look, and then she walked away. She left me, and I had no idea what to do or say.
To make conversation, I ended up asking the older woman if she liked dogs… It was all I could come up with, at the time.
#19 Clients Who Notice
I ran into a client at a local bar, and she asked if my boss and one of my coworkers were married. It was an odd question to ask, 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 to me that they were sleeping together. I ended up having to sit my boss down and let him know clients were asking about this. What made this situation even worse was that he would deny the affair to my face, even though I knew something was going on.
#18 Breaking Up And Moving In
My friend and I were moving in together, and his girlfriend was helping us move. While taking a lunch break, she decided to break up with him. After lunch, my friend was the only one who came back to finish moving. It was super awkward.
#17 A Scolding In Front Of A Teacher
I’m a middle school teacher, and one of my student’s parents brought him into my classroom one day- to shame him in front of me for his grades in other people’s classes. Apparently, since I was his favorite teacher, they just wanted me to be there while they yelled at him.
#16 Turned Down By A Twin
During my freshman year of high school, my friend (let’s call him Sam) and I had no homecoming dates. We discussed who we should ask, and we decided to ask these two twins at our school. We went to their soccer game to ask them there. Sam’s mom offered to drive us to and from 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 brushed it off, and said, “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 happily said yes. While we were hugging, I saw Sam talking to the other twin, and by no surprise she said no. He threw the rose and the sign he made into the trash and he stormed to the car, and I followed after him.
His mom could read the situation, and when she dropped me off at my house, the mom peeled away so fast I didn’t even have a chance to say goodbye.
Later on, I found out that he had asked out the girl I had asked, even though he knew that I had feelings for her. We are no longer friends.
#15 Movies At Work
I’m an IT specialist, and I manage all PC-related items for around 5,000 people and report to the Senior Manager directly. One day, I passed by someone’s office and I see this guy watching an adult video on his work laptop. I didn’t want to tell on him, but part of my job requires reporting all online activities, so eventually, I had to include this situation in my report. While I was submitting the report to my manager, I quietly discussed the situation. Come to find out, this guy had been written up before for watching Netflix, so this wasn’t his first offense. Knowing that he had been written up before made me feel a bit better, but nothing will erase that horrible memory of what I saw that day.
#14 An Unexpected Call
I was adopted as a kid, but I know my biological parents. I just haven’t talked to them since I was three years old.
I was sitting with my grandmother one day and the phone rings. I got to the phone first, and I answered it and brought it to where my grandma was sitting.
She talked to the person for about a minute and then handed the phone back to me. She said it was my biological mother, and she wanted to speak to me. I hadn’t spoken to her in about three decades.
Needless to say, neither of us had much to say to each other.
One of my friends wanted to go on a date with a “super fine girl” from Tinder; however, she had a requirement. Her roommate needed a date too, and if he could find her one she promised him that they could go back to her place early to get intimate.
So my friend came up with this 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 go with him, saying that she needed to leave too- due to her phone dying. For “convenience”, they would Uber back together.
I’m in full-out belly laughter at this point, but I wanted to go so I could see how this train wreck plays out. So I agree to go through with his plan.
While we’re driving on our way to pick up the girls, he grabs my shoulder and says, “Don’t slow down, and keep driving.”
I realized why he wanted to keep driving. Once we get to the end of the block, I discover that the two girls who were there waiting- were completely different from their profile pictures. We realized that we had just been catfished. I then had to drive my friend home while listening to him call this girl and her friend. It was awkward.
#12 A Scary Massage
One day, I decided to get a massage. While I was getting a massage, the massage therapist was discussing with me about her horrible 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 Problem
My mom has this strange theory that no one else in England speaks French, so she tends to talk trash about strangers- since she thinks they won’t understand. 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 told her in French to stop, because what she was saying was making me feel uncomfortable. She laughed out loud, telling me that English people only know “half a language.” The guy with the mustache then started talking really loudly to his friend in French.
#10 It Should have Been You
I was at my high school friend’s wedding. We were close, but we never dated. I was dancing with my fiancé at the reception, and the mother of the bride comes over to me crying, she pulls me aside, and says, “It should have been you.” Yikes.
#9 Single Parent Mishap
I was meeting with the chair of my department in college to fix a problem with my classes. I mentioned something about my mom being a single parent, and how that made things tough to balance. He heard me wrong and thought that I said that I was a single parent. He then gave me resources to help take care of my kids. By the time I realized what was going on, it was too late to say anything. He was just being so nice about it. It was uncomfortable.
#8 Sneaky Coworker
One of my (former) friends got me hired at the store she managed. She not only trained me incorrectly, but she also stole money from the register- and she blamed it on me. I was then expected to pay it back.
#7 An Unwanted Tattoo And An Unwanted Situation
I was working as a paramedic, and I was starting an IV on this older lady who had a thick Eastern European accent. I was finishing up, and she made a comment about my tattoos. She then said something about her own, so I asked what tattoo she had. She looked me straight in the eyes and said, “Well it was something I didn’t want to get.” I started to connect the dots — she was just about the right age to have been held in a concentration camp. All of a sudden the room turned cold. I didn’t know what to say.
#6 A Horrible Plane Ride
On an airplane ride; I had to sit next to my friends making out with each other, the band director was one seat in front of us vomiting, and the girl next to us was having a panic attack.
#5 Confessing To A Teenager
I used to babysit for a really nice young couple, when I was younger. One day, the wife discussed with me that she had been cheating on her husband. I believe that she just needed to confess to someone, but I saw her instantly regret the decision of telling me. I could see her thinking, “What am I doing telling a teenager in a small town?!” I was in shock, but I kept her secret.
#4 Picking Seats
At my cousins wedding I was the usher, and at the reception I had to send everyone to their seats. However, there wasn’t a seating chart- so I had to pick seats for everyone. I was also from out of town, and I had no idea who anyone was.
#3 A Tipsy Server
At a local bar, I experienced awful service. I had to wait an hour for somebody to come to the table, and another 30 minutes for my drink. The server then came to the table and started crying and complaining about the establishment. She was obviously tipsy and made everybody feel uncomfortable.
#2 The Burial Situation
I had to return something to an employer; and when I got there, he and three of his family members were burying his dog- who had just been run over. His mom blamed herself for it and got really drunk, then started hitting on me, making the employer feel very uncomfortable.
#1 (Un)Happily Snowed In
My boyfriend (of three months) and I decided to get snowed in together during a snowstorm, which granted us a long weekend off. The snow began to fall, and then a few minutes later someone came storming into his house. It was his girlfriend of five years. The snow got worse and no one was able to leave for over 24 hours. It was extremely awkward.