From Boyertown to Off-Broadway: Matt Freeman’s ‘The Ask’ Returns to the Stage

by Lesley Misko, Expression Staff

For Boyertown Area Senior High (BASH) graduate Matt Freeman, a play written about and inspired by his own working life is about to get another chance to engage New York audiences — this time Off-Broadway.

The Ask, Freeman’s two-character play about an ACLU fundraiser seeking a major contribution from a longtime donor, will begin preview performances Oct. 6 at Theater 555, 555 W. 42nd St. in New York City. Opening night is scheduled for Oct. 13, with the limited engagement continuing through Nov. 22.

The new production stars Marilu Henner and Shannon Purser and is directed by Jessi D. Hill. Tickets are currently on sale through the production's official website, TheAskPlay.com, which provides a link to the ticketing site.

For Freeman, the production is a return for a play that first reached the stage in 2024. The Ask premiered at New York City's Wild Project, where it ran from Sept. 6 through Sept. 28. Hill also directed that production, which starred Betsy Aidem and Colleen Litchfield.

Aidem's performance as Greta subsequently earned a Drama Desk nomination. Freeman lists that recognition on his website as part of the play's history. 

The play's second production brings a new cast to the two roles. Henner, a five-time Golden Globe nominee known for Taxi and numerous Broadway and Off-Broadway appearances, plays Greta, a longtime progressive donor. Purser, best known for playing Barb on Netflix's Stranger Things, plays Tanner, the young ACLU fundraiser who comes to Greta's Upper West Side apartment seeking a significant gift. The production marks Purser's New York stage debut.

The meeting does not go as Tanner expects.

As the conversation develops, the two women discover that their shared progressive politics do not necessarily translate into shared views about activism, generations, language, money or the responsibilities that come with supporting a cause. 

Playwright Matt Freeman, BASH 1994.

That conflict is at the center of the play — and it comes directly from Freeman's professional experience.

“So, my inspiration for writing was and is my own day job. I work as a fundraiser and have for almost twenty years. We all love the non profit organizations that make up our lives: schools, hospitals, organizations like Planned Parenthood, and even our churches, synagogues and mosques. Most of the funding for these things comes from individuals and is asked for by other individuals. These organizations don't pop fully formed out of the ground naturally. So I wanted to dig into those dynamics. I hope it helps people think about what asking for money really looks like; what having a job entails and what it asks you to compromise. And the play shines a light on those generational differences on the left that I think are really permeating the culture. Being on the same side doesn't mean you're always on the same side, you know?”

Concord Theatricals, which publishes the play, describes The Ask as a two-hander that examines the “power dynamics” involved in charitable giving. The company lists the play as a full-length drama for two adult actors.

The first production attracted considerable attention from theater critics. The New Yorker, for example, described the play as a look at the tensions within the philanthropic left, while other reviews praised Freeman's dialogue and his exploration of generational differences among progressives.

Freeman is looking forward to seeing the play interpreted by a different pair of actors.

“I'm excited for the play to return! It's complicated - this is a new production with a new cast and new producers so some of the things that were so successful the first round will necessarily change. But there's also something fun and exciting about giving two new voices a chance to interpret the play. Plus, these two actors have had incredible careers. I can't wait to show everyone how the sparks fly, even if the sparks have different colors.” 

Play available from Concord Theatricals.

For Freeman, the upcoming production is another milestone in a theatrical career that began well before The Ask.

Freeman graduated from Boyertown Area Senior High in 1994 and went on to attend Emerson College in Boston. He is now a Brooklyn-based playwright and director. His work has been produced at numerous New York venues, including The Brick Theater, HERE Arts Center, House of Yes, St. Mark's Church, Dixon Place, Access Theater and The New Ohio. He is a MacDowell Colony Fellow and New Dramatists alumnus, and he received the 2021 Kesselring Prize for playwriting.

The Kesselring Prize, awarded by the National Arts Club, came with a $25,000 award and a two-week residency. Freeman received the 2021 prize for Silver Spring, an autobiographical play about grief and family.

His professional accomplishments extend beyond The Ask. His plays and monologues have been published by Samuel French, Applause, Smith & Kraus and Playscripts, and his audio work has been presented at festivals including HearNow and Atlanta Fringe Radio.

But it is The Ask that will put Freeman's name back on a New York marquee this fall.

The production's return also gives audiences a chance to see how the play changes when two new performers take on its central roles. For Freeman, that is part of the appeal of having a play produced again.

For the playwright who graduated from BASH more than three decades ago, the journey from Boyertown to an Off-Broadway production is a source of pride, joy, and excitement.

The Ask at a glance

What: The Ask, written by Matthew Freeman
Where: Theater 555, 555 W. 42nd St., New York City
First preview: Oct. 6, 2026
Opening night: Oct. 13, 2026
Closing: Nov. 22, 2026
Cast: Marilu Henner and Shannon Purser
Director: Jessi D. Hill
Tickets: Available through The Ask's official website, which links directly to the production's ticketing site.

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