Every day is opening night.

Jenny Gersten

Jenny Gersten

Williamstown Theatre Festival’s Artistic Director, Jenny Gersten, joins us for our first On The Couch of the 2023/24 season. WTF has been bringing outstanding artists to the Berkshires for over seven decades with its diverse and thrilling summer festival comprised of plays, musicals, and cultural events. Additionally, with Broadway and off-Broadway Producing credits under her belt, she has built herself a name as a change maker and theatre visionary. Click below to read the full interview where she admits that at her roots, she’s a mom who’s still learning to sit in her incredible accomplishments.

What do you consider to be your best asset?
My optimism.

What was your proudest moment?
I know these are supposed to be showbizzy, but when I think about it, most of my pride stems from moments mommying my now adult sons. However, during the opening night of Alex Edelman’s Just For Us this summer, my kids stood with me at the party and urged me to recognize the achievement of doing something that was against the odds. They kept looking at me and saying, “Hey, look what you did” and seeing them be proud of me? That was crazy and deeply moving and memorable.

What is your favorite drink?
Seltzer with bitters and a squeeze of lime.

What is your favorite food?
Warm bread and butter

What is your favorite condiment?
I make a nice garlic aioli

What is your current obsession?
My new boyfriend

If you could give up one of your vices, what would it be?
Chocolate before bed

What is the one professional accomplishment you long for most?
Gonna keep this answer to myself

What is the one thing you waste too much money on?
Doesn’t everyone say taxis? It’s taxis for me.

What is the one activity you waste too much time doing?
Email feels like time wasted, frankly. I want to boycott email.

What do you consider to be the single greatest threat to your health?
What is this question? Oh my goodness. Maybe I don’t sleep enough.

What’s the single best trait you inherited or learned from your parents?
My dad was a hedonist, he took so much pleasure out of working and living.

What’s the single worst trait you inherited or learned from your parents?

What in the world most thrills you?
Finding and delivering joy. That sounds so goofy, but it’s true. I guess that’s related to hedonism?

What current trend in popular culture most irritates you?

What was the most embarrassing moment you’ve ever experienced on the job?
I do something embarrassing almost daily, I try not to hold on to it. But here’s a name-droppy story: One time at Williamstown, I was taking Bradley Cooper to see a house for his mom to stay in, and he offered to drive both of us on his motorcycle. It was my first time on a motorcycle, and as we sped off down Route 7 Bradley starts saying something through the wind and motor, but I can’t hear him. Two times I yell “WHAT?!” and then I hear him say, “TOO TIGHT!” — I was clutching him too hard and he couldn’t breathe.

What is your favorite place intheworld?
If I’m on a bicycle, I’m happy.

What is the most important trait you seek in a romantic partner?
Honesty, and sense of humor (in order to deal with all the honesty).

Do you prefer the company of dogs or cats?
Team dogs.

What would have to happen to make today the best day of your life?
Oh gosh, maybe a party where all the people I love show up and we get to laugh and sing and eat cake. Oh wait, that’s happening on Monday!

What is your personal motto?
Say yes.