“Awkward Conversations” by Alyson Herzig

This story appears in the anthology “Not Your Mother’s Book…On Working for a Living.” 

My background is in logistics, which is a fancy way of saying the business of everything from the manufacture of materials through the delivery to the final user. I have worked behind a desk, worn steel-toed shoes walking the warehouse, loaded trucks and managed a private trucking fleet.

Managing the private fleet of delivery trucks provided the most diverse group of people I have ever interacted with. I had 20 very different guys reporting to me. Some had just a few years of experience and others were 30-year veterans. Some were religious. A few were jerks, but most were not.

Initially, these guys had a difficult time accepting me as their boss. I can’t say I blamed them. I was younger than most of their kids and had never managed a fleet. But after some time, they realized that I valued their input, listened to their grievances, had their backs whenever needed, found solutions to their issues and was available at 2 a.m. when their trucks broke down on the side of the road.

Good communication helped to forge a bond with the guys that apparently let a few think I wanted to know the personal nuances of their lives that would be better shared with . . . anyone but me!

One of my favorite employees was an older gentleman named Milton. He was getting remarried after being a single man for more than 20 years. He came to me one day to discuss his need for some time off. After our conversation, I was pretty sure I wanted to crawl under my desk.

“Hey boss, you got a sec?”

“Sure, what’s up?”

“Well, you know I am getting married soon, right?”

“Yes, congratulations! Very exciting!”

“I need some time off before the wedding.”

“OK, you got vacation time coming to you.”

“Well, it’s not for a vacation—it’s for a procedure that my lady needs me to get.”

At that point in the conversation, I realized how horribly south it had gone. Panic started to set in. My eyes bulged. My heart raced. My only thought was, End. This. NOW! But I was trapped. I might as well have been Super Glued to my chair. There was no escape.

“You see, my man-parts are still all whole. My first wife didn’t seem to mind. However, before Mildred and I get married, she is requiring me to get a trimmin’.”

Holy shit! I was not prepared for that. There had been no training in business school—or life, for that matter—for the, “Hey, I’m going to get the old pencil sharpened” conversation.

“OK, well I don’t need the specifics. Just bring in a note from your doctor.”

Dear Lord, seriously?! This is NOT happening. I couldn’t even make eye contact with him at that point.

“I am gonna need a week or so off because, at my age, this is gonna be pretty painful. But she insists that if we are gonna have sexual relations, I need to have my manhood circumcised.”

I’m pretty sure I’m gonna die. Did I just throw up in my mouth?

“Yes, well . . . just go ahead and do whatever you need to do and put in for medical leave.” I waved him off, hoping to end the conversation as quickly as possible.

“I am mighty nervous about this and all, so I appreciate your understanding.”

I couldn’t end this talk quickly enough. I nodded and mumbled, “Yes, of course, best of luck, and take all the time you need.”

Milton exited stage left, leaving me trying to erase the horror of that conversation. It has now been more than 10 years, and it is still as fresh in my mind as if it happened yesterday.

My only hope is that Mildred appreciated the pain that poor man went through, because he needed almost two weeks to recuperate from his trimmin’.

I, however, may never recuperate.


Alyson Herzig is the co-creator of the anthology, Surviving Mental Illness with Humor, which will be available in 2015.Originally from New Jersey, Alyson now lives in the Midwest, but has kept her sarcastic, cynical Jersey attitude. You can find her blogging about the many disasters and observations of her life at TheShitastrophy.com.

Again, this story appears in “Not Your Mother’s Book…On Working for a Living.” The book is filled with 59 very funny stories by working stiff. Purchase this book today from your favorite retailer, Amazon (http://amzn.to/1yNYujU) or Barnes & Noble (http://bit.ly/1xXyrVR).

To submit your stories for consideration in future NYMB titles, go to http://www.PublishingSyndicate.com and click on the “Not Your Mother’s Book” tab.