When I was 10 I was invited to go to a Harvest Party by some family friends. A Harvest party is code for a Halloween Party and usually takes place at a church. This naming convention doesn't offend the fragile sensibilities of Evangelical Christians...but anyway.
I took a dress that belonged to my sister and a long dark brown wig and went as a girl. I thought this was a great costume and had lots of fun at school with it earlier in the day. That evening when we got to the church we all were rounded up to go to a nursing home to hand out treats to old folks. When we were done there we'd come back to the church and raise hell at the party. I didn't mind this because I like older people and always have.
When we got to the nursing home we went from room to room or person to person and handed out treats to them and brightened their day. This is when I discovered that my costume was becoming far less fun.
Most of the old folks didn't recognize me as a boy dressed as a girl...but rather just a young girl. I got plenty of "thanks sweetheart" and "what an adorable cutey pie" comments that made me realize this:
If no one gets the joke, then you're basically just cross-dressing.
That was the worst Halloween ever.