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The Most Uncomfortable Conversation You Had

Had to talk to an employee about complaints I was receiving regarding their body odor

My parents having the sex talk with me when I was in college and I spent most of the time correcting them on facts

Ask my mail lady to stop going #2 everyday in the bathroom if my office

I’m a bartender and this past weekend I had a couple flat out asked if I would have a threesome with them. I politely declined and they continued to ask me why

I get paid cash for babysitting and they forgot to pay me and I had to bring it up Which is the most awkward thing to say hey I love your kids but you forgot to pay me

I am an EMT and I had to talk to a 14 year old patient about being sexually active in front of her mom her dad her brother’s her sister and her great-grandmother then I had to ask her if there was a possibility she could be pregnant and everyone was just staring at her that’s lasted about 5 minutes before we had to barricade her into the ambulance to give her more patient privacy. Then the dad was staring in the back of the ambulance until we left 

Two days into my first full time job out of college I had to fire and employee for drinking on the job and had not met before. My first time meeting him was in a conference room when I had to let him go

Having “the talk” with my 12 year old son. He thought babies were pooped out

With my dad, a minister. Why my high school boyfriend decided to cut his hair and leave enough hair on top to have hot pink horns like Satan, gelled up and all

I kept getting complaints from my employees about someone on my team that kept playing with his “junk”. HR wouldn’t help, so I had to address the behavior

Surprising awkward conversation. When we told my in-laws that we were expecting they wanted to know who was on top during the act because they both think that determines the gender of the baby 

On Saturday I had the most awkward conversation. About a week and a half ago I got my DNA results and found out my dad is not my biological dad. I found my biological dad and we’ve been corresponding via email and text. Saturday we had our first phone conversation. We both kind of sat there at first not really knowing what to say. How do you start off a conversation with your 45-year-old daughter that you didn’t know existed until a week and a half ago? 

My awkward conversation was after getting wine drunk at Mariano’s I reached out to an ex best friend who I miss having in my life. When we talked when I sobered up she told me what a jerk I am and how selfish I am and how I single handedly ruined the friendship. Even though I lent her $500 that she never paid back

When we found out my dad was having an affair for 4 years while I was away at college. I met him for dinner at McCormick & Schmidt’s in oak brook. He proceeded to say “well I never fornicated with anyone besides your mother up until this point.” The waiter definitely heard too

Good morning! My most awkward conversation was had with my grandma- after my 2nd child was born she asked if i was planning on keeping my legs closed and enjoy life a bit without having anymore kids… said there are birth control options

WINNER: I own a music and movement program for toddlers. Parents complained that they could see a male teacher’s junk swinging around in his sweatpants

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