Didn't Know About The Divorce

I'm about to go for supper with my mom's new boyfriend, she's 50. I didn't know my parents were divorced.

- JustDax2341

The Invoice

My mom sent me an "invoice" for raising me. I hadn't spoken to her in 4 years at this point. I called her to see what was up. She told me that if I don't pay the amount of the invoice, she's going to lose the house she's living in. She lamented that I was an expensive child because I had so many health issues, and how she was owed this money.

I explained to her that I wasn't responsible for my birth or the complications during my birth that she caused. She cried until I hung up, then immediately called me back with stone cold composure and told me I was no longer a part of her family. Big loss there.

- pockyhockeysticks

Confronted By A Coworker

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.

- BigMilk0

Teacher's Erotic Poetry

My high school English teacher read us erotic poetry she wrote about her husband... who happened to be our History teacher.

- HotMagentaDuckFace

Five Minutes Of Faking It

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 house for dinner. I went and her mother asked me to say grace. Being a stupid 10 year old with no idea how to say I didn't know how, I clasped my hands together and mumbled under my breath for five minutes. *five minutes *. I probably would of gone long if the mom didn't stop me.

I didn't have dinner with them again.

- berrrrrrna

Sister or Best Friend?

Right, settle in and grab the popcorn, I've got a story for you. My sister married my best mate from college, it kinda made sense at the time because he had always been around at our house, spending time with my family etc. There were no hard feelings from me, I thought they were kinda cute and a couple. Anyhoo they get married had a huge reception were my parent spent an absolute fortune inviting probably close to 300 people, not just friends of my sister and her hubby but friends of my parents to show off to at how perfect the happy couple were.. Fast forward a couple of years and my sister and her husband had emigrated to a different country and out of the blue she calls me and asks if I can visit. So I pack my bags and go on holiday. When I arrive my sister tells me that she is getting a divorce from my mate and that she has been in a relationship with a lady on the sly for a year. So I've got my sister who now wants me to stay with her and support her through the divorce process and on the other hand I now have my best mate who is absolutely crushed as a male doubting his masculinity (as you would if your wife of 10 years just upped sticks and declared her self lesbian) who wants me to live with him and play video games and smoke pot with him every night.

I went and lived with my buddy. We got high every night, got drunk all the time and shagged everything.

I met my sisters new lady friend and we didn't gel. My sisters partner is almost as old as my mother is and I wish my sister all the best, but I struggle to connect properly with her new wife.

- cripplr-mr-onion

Acquaintance Awkwardness

An acquaintance was crashing at my place for a night. We went out and had a fun night out together, he ends up bringing someone home. I crash while they're enjoy each other's company. I hear the front door open and close in the middle of the night and figure she's gone home.

Around noon the next day, the guest bedroom door finally opens and I hear him walking down the hallway toward where I am in the kitchen. I'm pouring a cup of coffee for him when a FEMALE VOICE says hello.

Turns out it was the acquaintance that left in the middle of the night. He left the hung-over bar-girl in my house. She and I had an awkward conversation while she drank a coffee then left.

- milesmac

A Dramatic Reading

I was waiting in a school office to be interviewed for an Art teaching position in a middle school 7 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.

- Immoracle

Grindr Gone Wrong

Talking to a dude on Grindr and he invited me over. He started being way overly affectionate as soon as I stepped in the door. We had the typical "gay dudes about to hook-up chat" where we talk about work and how often we do this, etc. Things soon get hot and heavy. As soon as he was about to penetrate, he had a full on mental breakdown and started sobbing into my chest...

It went on for like 15 minutes and all I wanted to do was to get out of there! All I could do was reluctantly coddle him while he was hyperventilating over his recent breakup. We're both bare-ass naked, I've lost all libido at this point and I just prayed for him to get off me.

As soon as he calmed down, I don't think I've ever moved so fast in my life to get out of that house.

- nathanj594

Thanksgiving Dinner

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.

- Oregonguy1954

Grandma Is An Addict

My Grandmother is currently addicted to opiods. She frequently and often texts me asking me to take her to the hospital, effectively forcing me to tell her "You need to call 911." Even though I am almost always certain it's purely so she can go in and get her high. What's more, she tries to guilt trip people who won't take her anymore, including me, saying, "Oh I can't walk! It hurts so much I can't stand!" Except we all know it's bullshit because it only ever happens within a few days of her morphine refill. Also, the fact that her doctor recommends exercise and PT really doesn't help her credibility.

It's just so awkward having to tell my own grandmother that she's addicted, that she needs to stop going to the ER for things that aren't actually emergencies, and to actually do what the doctor tells her. It's so awful actually.

- continous

"Previous Experience" 

The guy I lost my virginity to married a friend from high school. That, in of itself, would have been whatever. The awkward part happened when she reached out to me for advice because she was a virgin and was sort of worried about his "previous experience."

She didn't know that previous experience was with me...

- MamaBee623

After We've Worked An Entire Shift Together

My boss makes me come in the room with her as a witness when she writes people up. It's awkward as f^ck because its usually after we've worked an entire shift together. I always make sure to tell them I had no idea and have nothing to do with it.

- TuesDazeGone

When Only One Of You Knows It's A Date

I was a freshman in college and a dude invited me to his place but worded it in a way that made it sound like other people would be there. I arrive in the same outfit I wore to band practice, and the dude opens the door wearing nice clothes. Shirt tucked in and everything. I chill with him, expecting more people would be arriving any minute, and they never do. Eventually a roommate comes out to get water and then goes back to his room. It eventually hits me that the guy is interested in me and this was some weird "date" thing. I was mortified. And in retrospect, it horrifies me that had he had really bad intentions, I willfully walked into a potentially dangerous situation. Luckily his intentions actually were just to chill with me. But I was BEYOND uninterested, and unskilled in the art of leaving places without feeling like I was rude. I think he could tell that I was caught off guard and he felt awkward as well. I mean he was dressed nice and I was in fucking band practice clothes. It was one of the most excruciating nights of my life. We had NOTHING in common and struggled for things to talk about. Cringing as I write this. Ew ew ew ew.

- Bethanyjcoolio

Grandchildren

Was hanging out with family. It was my 3 older siblings and their spouses as well as my brother who just had his first kid. That made me the only one without children. My mom proceeds to go on about how much she loves grandchildren and that I'm next and that I need to hurry up - while I'm sitting there with my girlfriend.

We had never really discussed kids at this point. I sat there having my family focus on me and ask all sorts of personal questions that I didn't want to be answering in front of everyone. It felt like an interrogation.

- SexBadgersaurus

Oh, THAT Kind Of Tattoo

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. I was finishing up and she made a comment on my tattoos on my arms and she said something about her just one tattoo and of course being friendly I asked what she got it of. She looked me in the eyes and said "Well it was something I didn't want to get" and of course I start connecting the dots and she was just about the right age to have been held in a concentration camp. It got real cold in that room all of a sudden. I had no idea what to say

- HeroShitInc

"A Foot And A Half From My Genitals"

A friend in middle school accidentally kicked me in the balls, and they swelled pretty badly. This resulted in me not being able to walk properly. This worried my mom enough that she had the doc check my junk out.

This wouldn't be so awkward if he hadn't handled my balls and had his face like a foot and a half from my genitals. I was about 14 at the time, and not the "biggest" dude. That's probably the most awkward situation I've ever been in.

- Justadudewithadeck

Caught Them Both Cheating

I caught my friend and his girlfriend both cheating with other people on separate occasions. I walked in on him and some chubby blonde girl bent over the toilet at a party - his girlfriend is a slim brunette. I walked in on his girlfriend with some black dude while I was visiting the two of them at their apartment. My friend is white and he was at work while his girlfriend was cheating. I promised both of them I wouldn't tell the other since that's not my place and I know their relationship is dysfunctional as f^ck.

The two of them started arguing one day over, surprise surprise, cheating. The both of them somehow caught wind that each other were cheating and they both started screaming at each other over it. I happened to be nearby so they both called me over. My friend said :
"Yo, you know this b!tch is cheating. Tell me who she's been f^cking!"

and she shouted:
"Don't listen to this as$hole. You know he's cheating on me. I know you've caught him before!" then pointed at me.

Neither of them knew that I had caught both of them cheating on each other.

I decided to maintain the middle ground and told them this wasn't my place to speak up. Then I quietly left while they continued to yell at each other. Knowing the two of them, an all out fist fight would have broken out between them so I decided not to say anything. They both ended up cheating on each other 2 more times, found out about both times and are still together for some reason.

- Merry_Dankmas

Hacking

Was sent by my boss to some people she knew to help with "internet stuff."

I learned on-site they wanted me to hack into their 13-year-old daughter's Facebook account because they thought she was up to something.

- TheFlipside

"Just Wheeled Him Over" 

I had to assist a friend of the family's grandfather with going to the bathroom. His daughter just wheeled him over to me and said "he needs to use the restroom" then left.

- SheZowRaisedByWolves