And then I told my boss...

Sometimes awkward, sometimes inappropriate, but always entertaining interactions with senior management that are too good to go unshared.

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So there.

Boss: You’ve got, like, something in your teeth.  It’s pretty gross.

Me: You’ve got, like, something all over your face.  It’s pretty stupid

Bigger than the Internet

Boss: Don’t punish me for being pedantic or I won’t explain these things and sometimes you won’t know what they mean. 

Me: Well I’ll just Google it then.  It’s not like all the information in the world stops with you.



Boss: You know, I’m not good at a great many things but I am good at being a Dad.

Me: That’s cute.

Boss: You’ll understand one day.  Hopefully sooner rather than later.

Me: Uh, what?

Boss: What, not there yet?

Me: Boss, I’m only going to be…

Boss: Right, right.  You’re 12, I’m ancient, forget it. 


From: Boss
To: Me
Sent: Sun 7/18/2010 2:52 PM
Subject: To be worn whenever my name is spoken


I mean, clearly.

From: Me
To: Boss
Subject: I’ll be in by 8:30

My alarm clocks are on strike this morning

From: Boss:
To: Me
Subject: Re: I’ll be in by 8:30

The security guys and I will miss you until you get in.

From: Me
To: Boss
Subject: Re: Re: I’ll be in by 8:30

Well, duh.  


Me: Yeah, I guess I’m not as murderous as I was last week.

Boss: Yeah, you were stinky.

Me: What?

Boss: Stinky.

Me: I SMELLED?? & you didn’t tell me??

Boss: You didn’t smell!  You were cranky.

Me: BRO.  Those are totally different things. 

Let Me Downgrade You

Me: I’m ordering mexican food - do you want anything?

Boss: Do you have a menu up?

Me: Sure do

Boss: How big do you think the tacos are?  How many do you think I could eat?

Me: Listen, this is assistant food.  The tacos are a DOLLAR. You could probably eat 4-5 of them.  This isn’t the Ritz Carlton, this isn’t that bougie rich people food you’re used to.

Boss: Fine, can you ask for an extra dosage of that fat that comes in a can?  That’s distributed by the government?

Me: Extra government cheese, too?

Sent in from Port Chester:

My boss just told me about his altercation with 2 old women & the Port Chester police department…

He had been getting from the local Dunkin Donuts & parked in a handicap spot. When he was walking out to his car an elderly man in a motorized wheelchair was circling around the back of my boss’ car, cursing. He didn’t think much of it and got into his car.

Cue the two older women who ran across the “street” (it’s basically a highway) from a McDonald’s and yelling at my boss as they dodged cars: “This poor old man! You blocked the ramp! You parked in a handicap space. Yap yap yap.”

Little did Boss-man know, the two older women had called the police. Police show and the women start complaining to the cop about how they believe my boss has a fraudulent handicap sticker..

Me: Did you show them your hands (he has no thumbs) or your brace?

Boss: I did something worse, I dropped my pants.

Turns out his leg was bleeding, he didn’t get into any trouble and as an ending remark to the two women he said, “I hope your life insurance policy isn’t paid up so when you die you don’t get the full benefit!”

Boss Angry, Boss Smash!

From: Boss
Sent: Thursday, July 01, 2010 3:59 PM
To: Me
Subject: May miss plane

Have to wait for QA so I can smack the current speaker. Stand by.


Me: Boss! I got tickets to Jay-Z & Eminem at Yankee Stadium!

Boss: Jay-who?

Me: You’re not that old.  You know who he is.  Actually, he’s not that much younger than you are.

Boss: Yeah but look at what he’s accomplished & then look at what i’ve done.  I feel a little inadequate.

Me: I mean, yeah, you’re not writing raps about production numbers & board meetings.

Boss: No! But I could start!

Me: Yo, my book game is so hard, you’re just hatin’ cause it ain’t your numbers my crew be paintin’.

Boss: Ugh, ugh, Biz Dev, word son.