Tell Us About Your Most Awkward/Inappropriate Work Moments! 37985

Remember when you were in high school (or possibly grade school) and there was nothing more exciting than reading the latest issue of Seventeen magazine?

Not for the fashions, of course—even then, you knew Urban Outfitters was crappy!—so much as for the not at all made-up “Say Anything” reader confessionals, which were typically some variation of how this girl was, like, fully making out with her crush during a game of Truth or Dare when, suddenly, she started spontaneously menstruating and then her ‘rents totally came home early and by Monday morning, all the popular girls in school were talking about it and it was, like, completely mortifying?

Anyway. Despite the fact that we’re all grown up now and (ostensibly) more mature, we’ve decided to get that first-person confessional goodness started up again. Except instead of your awkward almost-sex moments, we want to hear about your most painful/excruciating tales of intraoffice humiliation.

A few “hypothetical” examples, after the jump.

If you’re still having trouble thinking of any embarrassing work-stories [Ed: Really??] ask yourself the following questions:

Ever invite a gay plus-one to the small, semi-informal (but completely mandatory!) office holiday party only to have him brazenly hit on the boss’ 17 year-old son?

Or maybe you then shook hands with the boss of your small company at the very same party, only to have him politely introduce himself to you by saying, “Hello, I’m Mr. X. I don’t believe we’ve ever met,” never mind that you’ve been there six months already, fetch him his morning paper on a daily basis and sit diagonally across from him?*

Perhaps, you even accidentally blurted out something not quite office-appropriate (like, “Ew, no! I’m on the pill!”) in front of the company president? Or possibly you also unsuccessfully tried pulling a “George Costanza” and were nabbed sheepishly crawling under the desk of your 5-by-5 cubicle in an attempt to sleep off your hangover?

Whatever it is, we’d like to hear about it, so email us and share your worst work moment. All submissions will, of course, be entirely anonymous, and the winning entries will be reproduced and possibly awarded some yet-to-be-determined prize.

NOTE: The time you had the horrifying realization that your life was “just like Office Space” totally doesn’t count.

*Which would have been more aggravating, had it not absolved you of all responsibility in the gay plus-one/underage son fiasco.