Embarrassing Office Story Competition Winners

It’s been two weeks and now it’s time to draw the winners for the embarrassing office story competition!

As promised, I’ve republished the stories the winners submitted in this post. These are stories about embarrassing events, so as you’d expect some of these are a tad crude. My general opinion on office stories is: the cruder the funnier. If you disagree, this is definitely not the post for you to read! Just a warning.


Got my first big job and apartment in the city in April of 2005.  I didn’t know what to expect and only knew 1 person so you can assume that I was pretty nervous.  The night before I had a hard time sleeping and my stomach was anxious, but I was ready to take on the word, dark suit and all.

After getting through the HR paperwork, I met my boss who mentioned that she had to leave to meet a client that afternoon and the other remaining members of our team were out of the office on vacation, business, etc (I worked on a team of 4).  She offered to make it up by taking me to lunch when she returned.

So I decided to venture out downtown to try and find some lunch on my own and get the lay of the land.  I wasn’t too familiar with my surroundings and Arby’s was a familiar, slow-roasted friend from my past. Little did I know that this Arby’s was one of the most foul restaurants in all of the area.

After eating lunch, I decided I better use the restroom before heading back.  I had a little gas so I did what every self respecting man would do and tried to help it out.  As I pushed the door to the restroom, a shart (urban dictionary it) of career crippling consequences let loose into my new navy blue suit.  I nervously jumped into the stall to assess the situation (btw, the lock did not work on the door).  As I looked down in horror, I came to a cross-road.  I would be meeting many other members of the organization later that day and I could either pull them up and hope for the best and be referenced as the poop guy for the rest of my time there or maybe I could commando it.  I decided to take the road less followed.  I pulled off the underwear, gently folded them up into a square and placed them behind the basin of the toilet (this place didn’t even have trashcans in the johns).  I commandoed it across the street to Macy’s, bought one pair of underwear, changed in the fitting rooms and was back in the hour allotted to me for lunch.

To this day, I’ve never been back to Arby’s.


My very first job was as an Office Assistant with a prestigious advertising company. My role involved various office duties but mostly mediocre ones like getting groceries for the office, photocopying, running errands etc.

One day I was sent to go pick up the CEO’s Porsche 911 from the repair shop. ‘No problem’ I thought until I got there and discovered it was a manual drive with me only being able to drive an automatic. I rang up my boss in a panic and she quickly dismissed it saying ‘It’s easy’ and ‘I don’t have time for this. Just drive the damn thing back here’.

So I managed to crawl my way out of the repair shop, slowly crawl my way across town (stalling the car many times in the process) and make it to the parking lot at my work. Just as I thought ‘Victory! I’ve done it!’ I put the car into the wrong gear and slammed the car into the parking lot / office wall. Everyone in the office rushed out to see what had made so much noise and all raised their hands to their mouths in horror when they saw me in the CEO’s Porsche all smashed up.

I wasn’t fired and he had insurance so it was OK in the end. I did use the opportunity to remind my boss to never, ever make me drive a manual car for work again though.

Chris Offner:

I’d been hunting for jobs, and found one at a local community college in Texas; things were going well. I just graduated with my degree in Graphic Design, and things were looking up when I had met with the coordinator of the Student Activities department. We completed the interview, and everything had gone well. I got the job, and met me coworkers that share my office. One of them, I’ll call “S” (in her early 40’s), sits right behind me, while the others are nearby, in clear eyes view.

“S” is a competent user of Windows Live Messenger, and was chatting with a friend of hers over matters foreign to me. “Girls…gosh” I was thinking, but my photoshop project had reached a halt. I needed a bit more information before I could proceed. I turned around to ask her a question, and we got in a heated conversation about working here, and problems that we face, when I notice her monitor blinking. My eyes wandered around the room, and finally made their way to her monitor. Her friend, (who’s name I could see) had sent her an instant message, “He’s just jealous because he doesn’t have a big cock like this one”. I tried to act coy, but she noticed that I was looking behind her, and when she turned around to see what I was looking at, she exited the Instant Messaging window as fast as she could and we both started laughing hysterically for the better part of 10 minutes. She explained to me that her friend had tried to send a picture of a “well-endowed” man to her husband, and it had never gone through. She was interpreting his lack of response as anger, and was explaining her point to “S”.

Needless to say, I now ask if I can turn around before I ask her any questions face to face.

Enjoy your prizes, guys.

If you missed out on winning this time, Embassy Suites Hotels is running a competition that’s similar — you post your most embarrassing office party stories. The winner will receive an office holiday party at Embassy Suites (that’s a little fancier than a file folder with attitude!).

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Joel Falconer is the co-founder of public relations company Methodic Studios, publishes the gaming blog StartFrag, and is an editor at leading technology news site The Next Web. You can follow him on Twitter.


  1. Nokadota on the 18th November

    Ahahaha, these stories are pretty funny.

  2. Anton Ranestam on the 22nd November

    Really good and funny stories!

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