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The Craziest Things People Actually Said To Their Bosses.

By Robbie Woods
January 19, 2018
Shutterstock / Ekaterina Vidyasova

1. A bunch of the staff was sitting in the cafeteria. I was 22 and in my first job. My boss, who was often inappropriate, asked if I was still dating this guy. I answered, no, we broke up.

He looks around to make sure everyone is listening. “Well, what are you doing for adult satisfaction?” he asked. Everyone laughed.

I was not going to take this from him. I come across as the type of person who wouldn’t say crap if I had a mouthful of it, but I was raised to stand up for myself. I looked him in the eye and answered, “Well, Bob: I play with myself. I bet you know a lot about that.”

Everyone roared. I think he realized he crossed the line. He actually called me at home later and apologized.

Pat Powell

2. I was an 18-year-old private in the military, and found myself with a new position driving the company commander around in a military jeep. We were on a training mission ‘in the field’ and I was driving the commander and three of the sergeants were in the back seat.

The commander was in a good mood and says, “Trumeter, isn’t it wonderful the government pays you great money and all you have to do is drive a jeep?”

“Yes,” I said, “but they pay you so much more and you just sit there.” The sergeants were laughing for hours. The commander not so much!

Darren Trumeter

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