The play depicts a battle of wills between a young progressive ACLU fundraiser and a longtime donor.

Marilu Henner and Shannon Purser will star in the return engagement of Matthew Freeman’s The Ask, which is set to begin preview performances off-Broadway at Theater 555 on October 6, ahead of an official opening night October 13. Performances are scheduled through November 22.
The play depicts a meeting between a longtime ACLU donor on the Upper West Side (Henner) and a young progressive agent of the organization (Purser) sent to secure a significant gift. Through their exchange, Freeman exposes the cultural and generational rifts on the American Left.
Jessi D. Hill directs the production.
Henner was last seen off-Broadway in The Journals of Adam and Eve. Purser played Barbara Holland on the hit Netflix series Stranger Things. The Ask will be her New York stage debut.
The production will feature set design by Craig Napoliello, costume design by Nicole Wee, lighting design by Venus Gulbranson, and sound design by Ben Scheff. Casting is by Geoff Josselson Casting. Adam Cohen is the producer.
The Ask made its world premiere in 2024 in a production (also directed by Jessi D. Hill) by Theater Accident at the Wild Project. TheaterMania’s review described the play as “an invitation to really hear someone, even if you still walk away disagreeing.”