Every day is opening night.

Jenny Gersten

Jenny Gersten, Williamstown Theatre Festival’s Artistic Director since May 2010, prepares this week for WTF’s New York City benefit taking place on Monday, November 18th honoring beloved Williamstown director, Scott Ellis. 2014 marks this Berkshire theatre’s 60th Anniversary season. Gersten, who served as Associate Producer of WTF for 9 years, Associate Producer at The Public Theater, and producer of six Shakespeare in the Park productions, among other things, is headed to Friends of the High Line where she will bring her special theatrical flair to serve as their Executive Director this coming January. Until then, find out what trills her most when we get her On The Couch!

What do you consider to be your best asset?

I think my modesty is awesome. 

What was your proudest moment?

The births of my kids were about as proud as I have been, but the amazing thing is, they get better every day, which just makes me more crazy proud.

What is your favorite drink?

Sidecar at Bar Centrale, but only on very special occasions because they are so delicious and so strong.  I drink tea every day.  I'm drinking tea right now!

What is your favorite food?

Hot fresh bread and cold butter.

What is your favorite condiment?


What is your current obsession?

Right now I'm obsessed with biking (both in the city and soon to be obsessed with road biking), PigPen Theatre Co, and my new job at the High Line. 

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

Email.  Does that count as a vice?

What is the one professional accomplishment you long for most?

It would be great to look back and say what I did that one time was very helpful to many.  What that will be I don't know yet.

What is the one thing you waste too much money on?

Taxis.  Does everyone say that?

What is the one activity you waste too much time doing?

Thinking about all the stuff I'm not doing.

What do you consider to be the single greatest threat to your health?

Mean people.

What is the single best trait you inherited or learned from your parents? 

Love for and belief in creative people and not-for-profit organizations.

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

Love for and belief in creative people and not-for-profit organizations.  Why couldn't I be a broker???

What in the world most thrills you?

Passion.  Not in that way, but when I see someone passionate about something, I think it's thrilling.

What current trend in popular culture most irritates you?

Devices.  I wish we all looked up and out and at each other more.

What was the single most embarrassing moment you've ever experienced on the job?

When Bradley Cooper told me I was holding him too tight on his motorcycle.  #humblebrag

What is your favorite place in the world?

Bolinas, CA.

What is the most important trait you seek in a romantic partner?


Do you prefer the company of dogs or cats?

Dogs. We are getting our first one  – a black lab – in a few weeks.  I'm really excited and slightly terrified.

What would have to happen to make today the best day of your life?

I'm so focused on Williamstown Theatre Festival's gala right now.  I think if Liza Minnelli called to say she would sing at our benefit on Monday, it would be the best day.  Can you help with that?

What is your personal motto?

Take care.