Category: Drunk Boss

Hard Sleeper


I work in a job where I have to travel all the time.  I’m literally on the road three weeks out of every month.  It’s not a bad job and I love the hotel/airline/credit card rewards. My boss is not a bad guy, but he is a little strange to travel with.  Luckily, I only […]

Limo Man


Was in Vegas for a work conference with my boss last year.  Admittedly, whenever I’m there, I don’t mind going out and having a little fun.  I figure, it’s Vegas!  However, this trip provided just a little more fun than usual. After some drinks and gambling, a bunch of us hit The Strip.  My boss […]

Bar Hopping


Was at a local bar with a few male buddies.  One of my buddies said he was going to the bathroom and ended up disappearing for quite a long time.  In fact, after an hour, we started to wonder where the heck he was. He finally came back and had this amazing tale.  He had […]

Was I Here Last Night


My boss is the Controller of our company.  He’s a little quirky, but overall, not a bad guy.  Once in a while, we have to travel together for work. Whenever we travel, my boss has his routine.  It’s always the exact same thing.  Go to meetings, then find a bar to play billiards, then drink […]

Her Life Story


My boss is the kind of person who will tell you her entire life story in the first five minutes that you meet her.  Literally.  Based on the industry we work in, we are out and about a lot; and it’s mortifying when she starts in on her ‘story.’ Imagine this.  You meet her…you introduce […]

Big Spender


My boss called me into his office a few weeks ago and said that he had the company tickets to a MLB baseball game.  They were tickets in a suite! I consider myself a peon and I never see the corporate tickets.  My boss had never been given them either.  So needless to say, we […]