One. That is the amount of times, before last week, that I had done stand-up comedy as Jessica. When I began my journey in the world of comedy in 2010, I didn’t know how to incorporate my feminine side into, but I knew that I wanted to.
The fact is, though, that it is tough enough getting on stage and preparing to tell jokes to a room full of strangers without compounding it with the whole “dude in a dress” factor. I was starting to think I’d never get to hit the stage as Jessica again, until I got a phone call.
My wife and I had just finished up a seven-mile run (we are training for a half-marathon) when I saw a message from one of my comic friends. Once I called him back and he informed me that he was putting on an all female stand-up comedy show and wanted me to host it in drag.
Without hesitation, I accepted, knowing that the days leading up to the show would be nerve wracking. Not only would I need to find an outfit but I’d also need to prepare an ten minute joke set and find a way to document the whole thing for my blog and YouTube channel.
Some of my other buddies heard about this and asked me about it. I acted as if it was no big deal, but on the inside I kept going back and forth between excited and ready to quit. It’s not that I wasn’t confident, it’s just that it had been so long since I did stand-up en femme.
I did my best to prepare for the night, linking up with my friend (and the headlining comedian) Sandra Mirocha. We talked about the jokes I told last time I was on stage in a dress as well as some newer concepts I had been kicking around. Together, we wrote a few jokes for my set.
In addition to actual comedy material, my wife bought me a pair of heels (more on that later) to go with my brand new off-the-shoulder dress from Express. All that was left to do was wait.
When the day arrived, the butterflies kept creeping into my stomach. As time progressed, I questioned myself more and more but because of the commitment I had made, I knew that I couldn’t just bow out. So I resolved to do the best I could do and not worry about anything else.
After a three mile run I hopped in the shower and began my transformation. Two hours later, my wife is driving me to the venue and I can just hear the voices in my head telling me to turn around and go home. Thankfully, my wife was helping to encourage me and calm me down.
Once I got to the club, the female comics (with whom I am friends) were very impressed by my appearance. A couple of them had seen me in drag before and a couple of others were seeing me for the first time. Everyone else was very cool about it, and shortly thereafter, I kicked off the events of the evening.
This brings me to some bad news and some good news. On the bad end, I didn’t come away with any pictures of myself from that night — I was so nervous and occupied with doing a good job that it completely slipped my mind. On the good end, however, I did film my entire set and will put up bits and pieces in a few days. Also, while I didn’t do as well as I would’ve liked to (though part of that was lack of preparing my material) I was still somewhat happy with my performance.
The next day, I had a strangely depressing feeling. It took me a while to figure out what was bothering me, and I’d like to share it with you. Perhaps you can offer me some advice or suggest some action. I know that I want to do more stand-up comedy as my female self, but I don’t really know how to go about it.
One option is to choose one or two nights a month that I normally perform and instead of going up in guy mode I could go up in drag. I’d also love to perform comedy at the various transgender conferences across the country. Other than that, I could film my sets and put them all online, trying to increase my Internet fan base.
The toughest part is not actually dolling myself up but rather getting the jokes together and making sure that they are funny. It’s very difficult to perform my regular proven material when I’m wearing heels and a short dress. Also, I’m not sure the audience is going to buy it. At the very least, I need to reword some of them before telling them as Jessica.
This is why I’m writing jokes specifically for my drag comedy sets, and jokes need to be told several times before they become good. Who knows when the next show will be, but I’d love for it to be soon and I’d be ecstatic if one day I could be doing this on a regular basis.
TL;DR: I did comedy as Jessica for the first time since November 2010 and it went okay. I want to do it more but am searching for the right way to go about it.
In the comments feel free to share your advice as well as any time you have performed as your female self.
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