Today is not Halloween, but at my office, it is.

My boss loooooooooooves Halloween, and a few weeks ago, an email went out saying that we’d be having our costume contest today, and it was MANDATORY. (Emphasis hers.) Of course, Halloween isn’t until Sunday, and in my opinion, there are two times you should be exempt from celebrating Halloween at your place of business:

  • If it falls on a weekend, or

  • If you’re an adult

Of course, if Halloween falls on a weekend and you choose to celebrate it at work anyway, the natural thing to do is to celebrate it on the immediately preceding Friday. But my boss is going to be out of the office tomorrow, so she’s making us do it today. All of us.

So that means we’ll be the only people in our building the city the world who are dressing up today. We’ll even be having a costume contest, judged by impartial strangers dragged in off the street. There will be three categories: funniest, most creative and, ugh, sexiest.

“I know you’ll be my main competition for sexiest, Jerry!” my boss said to me the other day.

Double ugh.

The costume contest will be followed by a pizza party. Anyone who doesn’t dress up, in addition to being ridiculed and harassed, isn’t allowed to have any pizza. Trust me, she’s very serious about this. I haven’t dressed up for Halloween in about 25 years, but when the boss says it’s MANDATORY, it’s MANDATORY.

My initial thought was to wear something inconspicuous, so that anyone who knew me would know it was a costume, but anyone who didn’t know me would just think I was a regular guy.

Yes… (embarrassed chuckle)… I’m going as a straight guy.

That shirt, if you can’t read it, says “Flowers: $20… Dinner and a Movie: $60… Taking her back to your place: PRICELESS!”

And it suddenly struck me that I have to wear this shirt all day, and that people who don’t know me will definitely not think I’m a regular guy. So much for being inconspicuous.

Did I mention this is all being videotaped?

Wish me luck.

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