Penny: For Your Thoughts


Dating is hard. Dating while old is harder. Dating while old and transgender? Welcome to the ShMILF LIFE. Award-winning comic storyteller Penny Sterling's autobiographical one-woman play about trying to discover her femininity and sexuality in a society that continually "others" her".




55 minutes




Thu 7/21 @ 8:00PM
Fri 7/22 @ 5:30PM
Sat 7/23 @ 3:30PM



Stand-Up Comedy

Recommended For

Ages 14+


One Person Show, Performance Art, Stand-Up Comedy


Discussions of sexuality, discussion of sexual assault


ShMILF Life_Main_Square


ShMILF Life is me, waiting in a coffeeshop for my date to arrive (remember doing that?) and talking to the audience while I'm waiting. I tell stories about how I got to this point--about discovering who I am, who I was interested in, who was interested in ME, and what they were interested in doing with me--which was not at all what I was interested in. Mostly. ShMILF Life is me trying to find an authentic view of who I am and who I want. ShMILF Life is trying to find a satisfying relationship in a world that assumes much about who I am. ShMILF life is about rejecting fetishization. ShMiILF Life is learning that things that feel ONE way to a man, feel entirely different to a woman.
But above all, ShMILF Life is pretty freaking hilarious.

Written & Performed by Penny Sterling

Penny Sterling - Writer & Performer

Penny: For Your Thoughts


Explore our hashtags across your favorite social platforms:

#PennySterling #ShMILFLife

Additional Info

Penny Sterling says serious things in a funny way. And sometimes vice-versa. Penny’s storytelling career began in 2016, with her first play Spy in the House of Men: A One-Woman Show with Balls, which she wrote in response to being asked so many questions after transitioning in 2015, when she was 55. What she thought would be a one-off performance turned into a small sensation, and Penny has now performed Spy more than 40 times, as far west as Minneapolis, as far east as Washington, DC, as far south as Richmond, and as far north as…

Well. That would be Minneapolis, again. Penny obviously didn’t think this through.

Penny’s next show, Parents & Children, Husbands & Wives, (a collaboration with actual husband & wife musicians Mike & Mel Muscarella) was performed at the inaugural Border Light Fringe Festival in 2019, to great acclaim, and many Dunkels, since it was at the Hermit Club.

ShMILF Life is Penny’s third (and arguably funniest, but who wants to argue in this heat?) show. She’s also created a fourth show: Someone No One Can See, a collaboration with PUSH Physical Theatre, created in part by grants from the National Endowment for the Arts, the NY State Council for the Arts, and the LGBTQ Giving Circle, and she’s gonna work like heck to try and get that show to Cleveland as well.

When not performing, Penny is a freelance video professional, and an adjunct professor teaching Public Speaking and Sports Video Production (2 separate courses) at St. John Fisher College in Rochester, NY.

Penny lives in a crooked little house in Swillburg with Betty the Cat, who is as unpleasant as she is photogenic, and no, we’re not making any of that up.

Photo Credit(s): Kerry Blauvelt