Last summer I went to Chicago to study at the Second City. I was taking a weeklong intensive improv class with two of Chicago’s most talented teachers.

The week took place during a small window of feeling, if not great, decent. Stuff was soon to be really really not decent. But this week, this class, was eighty kinds of awesome.

One of the two teachers was Rachael Mason. Rachael has the amazing ability to come off as both a tough bitch and super supportive at the same time. It’s a kickass talent.

We did an exercise where we moved around the room and it helped inform our character. I don’t know how it happened but the character I was supposed to play was a dainty woman.

After the exercise Rachael asked how it felt. I said on stage I was always uncomfortable playing a,woman. She paused, looked at me, and said “That’s the most fucked up thing I have ever heard.”

The super supportive tough bitch was right.

I spent the next few minutes saying things like “I mean it’s not like I want to be a guy or anything.” and “You see I have a deep voice and hate pantyhose.”

These moments were the most honest I have ever had in an improv class. I felt exposed but never judged. It was like being a first-timer in a nudist colony.

Tonight, a year later, I decided I would play only women on stage. This was a challenge. I frickin have breasts and a vagina yet am more comfortable being a dude on stage.It requires less vulnerablity and truth.

But I did it. It was not some eye opening, life changing, amazing show. I pushed myself but nowhere near as much as I could have.

But I did it. I played all women. Some even had lady feelings and at times I actually felt feminine. And, believe it or not, I survived. Yay, estrogen points for me.

To quote Mason, my vagina weeps.