Matthew Freeman’s two-hander The Ask moves up to a commercial Off-Broadway run at Theater 555, where previews start on Tuesday, October 6, with Marilu Henner as a wealthy donor and Shannon Purser as the fundraiser sent to win her over.
The whole play takes place in an Upper West Side apartment. Greta (Henner) has given to progressive causes for decades; Tanner (Purser) is a young ACLU fundraiser who has come to ask her for a substantial donation. The two ought to be on the same side, and for a while they are, but the conversation keeps snagging on assumptions neither of them shares, and what begins as a courtesy call turns into a contest over which generation gets to define the cause.
Freeman knows this room from the inside, having spent more than ten years raising money for the ACLU himself. Jessi D. Hill, who directed the play’s earlier staging at the Wild Project, returns to direct. That downtown run was well received: Time Out New York gave it four stars and a Critic’s Pick, describing “an entertaining and empathetic examination of generational and philosophical differences that divide the political left,” and The New Yorker found in it “a distressing vision of the philanthropic left.”
Henner, a five-time Golden Globe nominee, is coming back to the New York stage. Purser, the Emmy nominee whom most audiences know from Netflix’s Stranger Things, is making a New York stage debut in the role of Tanner.
The design team is Craig Napoliello (sets), Nicole Wee (costumes), Venus Gulbranson (lighting) and Ben Scheff (sound), with casting by Geoff Josselson Casting. Adam Cohen produces. General management is by Jessica R. Jenen for JRJ Productions LLC and Staci Levine for Groundswell Theatricals, Inc.; Jenen is also the executive producer.
Opening night has moved to Thursday, October 15, 2026, a change from the date first announced. The limited engagement runs through Sunday, November 22, 2026, at Theater 555, 555 West 42nd Street, and tickets are on sale through the production’s website, TheAskPlay.com.
