

Photo credit: Marilu Henner and Shannon Purser in The Ask off Broadway. (Photos by Joan Marcus)
'The Ask' Off-Broadway review — two generations debate a donation
Read our review of The Ask off Broadway, a new play written by Matthew Freeman, directed by Jessi D. Hill, and starring Marilu Henner and Shannon Purser.
Summary
- The Ask follows a contentious meeting between a young ACLU fundraiser and an older, lapsed donor who feels the organization's values have changed
- The show is recommended for fans of stars Marilu Henner and Shannon Purser's TV work and fans of stories about how different generations approach sociopolitical issues
Of the many quibbles Greta (Marilu Henner) makes in Matthew Freeman's new play The Ask, her irritation with the sheer number of emails she receives warrants a bit of sympathy. Even for people who try to keep their inbox at zero, the landslide of messages from charities, nonprofits, and other organizations cements how impersonal the current age feels, and how easy it is to compartmentalize conversations and debates about real, important issues into the intangible digital world.
Although Greta has a range of topical talking points she can lob at Tanner (Shannon Purser), the young, unsuspecting ACLU fundraiser who’s come to Greta's apartment seeking a donation, the older, wealthy feminist’s feelings are so raw that their conversation about “gift giving” rapidly reveals how personal the endeavor is.
Greta feels abandoned by the ACLU; the previous fundraiser she had worked with left, and the organization’s language and priorities have shifted to concerns Greta believes to be off track from its original mission to defend constitutional and civil liberties. But the minutia feels more like a smokescreen for both Greta’s feelings of being left behind by a younger generation of social justice advocates and, more specifically, by an ACLU that simply didn’t bother contacting her during the staff transition.
Henner does a solid job conveying this dual mindset. Despite her annoyance, she has the resources and power to help the ACLU and telegraph what’s annoying her: the feeling that her relationship with the organization was one of convenience and the growing dissonance between their values and hers. Although Henner’s character work is slight, her belief in Greta’s complicated, sometimes petty feelings nonetheless seems real and of the moment. Purser is strangely relegated to maintaining a soft, frictionless, and inoffensive tone that is at first useful, but then betrays a lack of variation both in the performance and in the play itself.
Director Jessi D. Hill doesn’t quite nail the game-like aspect of the pair’s meeting: They both want something from one another, and they’re trying to play one another to get the best hand. For Greta, an acknowledgment that the older generation is right about contemporary social issues, and that she's a good donor, is valuable to progressive politics themselves. For Tanner, a sizeable gift and validation of their own efforts to secure it is crucial for the forward motion of a new generation fighting the good fight.
But Matthew Freeman’s play, seemingly in an effort to paint both characters fairly, defangs the tension between them. The play gestures toward compelling conflict, more political than personal, without ever escalating it. Thus, the stakes — between these two people as individuals and as symbols of braoder differences in political engagement, wealth, and generation — never feel urgent or exciting, even with two people showing down.
The Ask summary
Tanner, a young ACLU fundraiser, has a tricky conversation with Greta, an older donor whose gifts lapsed the previous year. As they explain the types of financial assistance Greta can offer, Tanner realizes Greta has more grievances up her sleeve than expected, and the two debate the future and meaning of the ACLU.
What to expect at The Ask
The Ask is a traditional two-hander, and their showdown is only verbal, with Henner and Purser mostly sitting. Henner gives Greta a physical antsiness that provides a little dynamism to the staging. Craig Napoliello’s set is a narrow corner of Greta’s Upper West Side living room, but the decor — Cindy Sherman photos, coffee table books — adequately conveys the bougie kind of person she is.
What audiences are saying about The Ask
On the review aggregator Show-Score, The Ask has a 71% audience approval rating, averaged from 25 reviews, as of writing. Theatregoers have shared mixed responses to The Ask's central conflict and performances.
- “An interesting look at the age old question: can a monetary price be put on good intentions?” - Show-Score user Richard 129440
- “A two-character play that TEASED the audience with the tip of the iceberg of a subject matter, but that never really addressed the real suject matter – OVER INCLUSION vs SINGULAR FOCUS on a particular issue.” - Show-Score user Marc 7104
- “Loved the intimacy of the play and the theater. Acting was top-notch and found it very interesting and relevant.” - Show-Score user Monika K
Read more audience reviews of The Ask on Show-Score.
Who should see The Ask
- Fans of Shannon Purser's Emmy-nominated performance on Stranger Things will enjoy the actress making her stage debut and the careful tone of voice she exhibits when trying to get a large donation from a wealthy patron.
- Marilu Henner has graced stage and TV screens for years, and fans of her work will enjoy her wit and sense of immediacy in the show.
- Theatregoers interested in intergenerational stories and conflicts will enjoy how the play examines how older and younger people navigate tricky political and social questions.
Learn more about The Ask off Broadway
Although The Ask poses interesting questions about generational political differences and wealth, framing them through a two-person showdown, the play never amps up the stakes enough to go all in on the drama.
Photo credit: The Ask off Broadway. (Photos by Joan Marcus)
Frequently asked questions
How long is The Ask?
The running time of The Ask is 1hr 15min. No intermission.
Where is The Ask playing?
The Ask is playing at Theater 555. The theatre is located at 555 W 42nd St, New York, 10036.
How much do tickets cost for The Ask?
Tickets for The Ask start at $64.
What's the age recommendation for The Ask?
The recommended age for The Ask is Ages 13+..
How do you book tickets for The Ask?
Book tickets for The Ask on New York Theatre Guide.
Is The Ask on Broadway or Off-Broadway?
The Ask is playing Off Broadway.
How long is The Ask running?
The Ask currently has tickets available through 22 November 2026. Check calendar for availability.
Who is in the cast of The Ask?
The cast of The Ask includes Marilu Henner (as Greta) and Shannon Purser (as Tanner).
Who directed The Ask?
The Ask is directed by Jessi D. Hill.
Who wrote The Ask?
The Ask was written by Matthew Freeman.
Originally published on
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