Notes on Going to Work Dressed as a Woman on Halloween
I did it seven times. The last time was ten years ago—my final Halloween at work before I retired.
It still amazes me that so many of my co-workers had no idea who I was until I spoke. Even then, a few still did not put two and two together.
And when I ventured out among civilians on those Halloweens, I think most people had no idea I was a guy.
One Halloween, I went to Stop & Shop during my lunch hour to pick up a few groceries. I checked out with a cashier whose line I had been through many times before. In boy mode, she was always cool and businesslike with me. In girl mode, she was positively friendly.
On another Halloween, I went to a restaurant for lunch by myself. The waitress was friendly and professional, but she never mentioned my “costume,” even though she gushed over the costumes worn by a couple sitting nearby.
After paying my bill, she returned with my change and I asked, “How do you like my Halloween costume?”
She gave me a blank look.
“What is it?”
“I’m a guy.”
She was shocked. She had had no idea! Then she began gushing over my “costume,” telling me how much she loved my hairdo—actually a wig—and how “cute” my nails were.
That was a very happy Halloween!




