The Ask

The Ask is a drama for two actors by Matthew Freeman, staged Off-Broadway at Theater 555 on West 42nd Street. A longtime supporter of progressive causes opens her home to a young fundraiser from the American Civil Liberties Union, who has come to secure a large gift. The whole play is that one visit: a single conversation in a single scene.

It is an original play, not adapted from a book, film or earlier stage work. Freeman wrote it out of his own years as an ACLU fundraiser, so the relationship between donor and asker is drawn from the inside. This engagement is a return of a play first staged in 2024, billed as strictly limited, and described as the first commercial Off-Broadway production of the script. Adam Cohen is the producer.

Two ideas run through the text. One is the distance between generations and cultures on the American left. The other is the uneven footing of a wealthy donor and the person whose job is to ask her for money.

The action is set in December 2022, in Greta's apartment on Manhattan's Upper West Side. Greta, in her early 70s, is a liberal feminist who gave to the ACLU for decades until she stopped in 2021. Tanner, in their late 20s, is non-binary, uses they/them pronouns and holds the title of Gift Planning Officer at the ACLU. Tanner has come to find out why the giving ended and to win Greta back with a major gift.

Greta has her reasons. She feels the organization has drifted away from civil liberties and into a long roster of progressive causes, and she points to student debt forgiveness as an example. There is a personal grievance too: her longtime contact there, Carol, left without a word to her, and Greta suspects layoffs.

Reproductive rights matter most to her, so language becomes a flashpoint. The inclusive wording Tanner uses for people who can become pregnant is a sore point between them.

Because Tanner needs the gift, Tanner cannot push back as freely as Greta can. That imbalance shapes the whole conversation.

Freeman wrote the play as a two-hander, so everything rests on the exchange between Greta and Tanner. The licensor lists it as a full-length drama, and Concord Theatricals (Samuel French) licenses it. The script is largely the same as it was in 2024, and Tanner still uses they/them pronouns in the 2026 staging.

The 2026 set is the well-furnished drawing room of Greta's Upper West Side home. Hill, Napoliello and Wee return from the 2024 production, while Gulbranson and Scheff are new to the play.

As of October 2026, Marilu Henner plays Greta and Shannon Purser plays Tanner, with Julia Brothers as Greta's understudy. Henner is a five-time Golden Globe nominee whose television work includes the sitcoms Taxi and Evening Shade. On Broadway she has appeared in Grease, Chicago and Pal Joey, among others, and her previous Off-Broadway outing was The Journals of Adam and Eve. She has Highly Superior Autobiographical Memory and tours her own solo show.

The Ask is Purser's first New York stage appearance. She played Barb in Stranger Things, a part that earned an Emmy nomination, and Ethel Muggs on Riverdale, and she first took the stage in La Cage aux Folles at the Pasadena Playhouse. Casts can change during a run, so check the official show website for the latest.

The world premiere took place at The Wild Project, 195 East 3rd Street, and Theater Accident produced it together with The Flying Carpet Theatre Company. It played from September 6, 2024 to September 28, 2024, with Betsy Aidem as Greta and Colleen Litchfield as Tanner. The two had acted together on Broadway in Leopoldstadt. That version ran 80 minutes with no intermission.

The Off-Broadway return began previews on October 6, 2026. Opening night was first announced for October 13 and later moved to October 15, 2026.