A veteran donor and a young fundraiser lock horns over the biggest gift of her life in a single Upper West Side living room, and that tense afternoon is now playing out eight times a week at Theater 555 in Manhattan. Marilu Henner and Shannon Purser star in Matthew Freeman's two-person play The Ask, with Purser making her New York stage debut opposite Henner's five-time Golden Globe-nominated turn as the donor holding the purse strings.
A Two-Hander With High Stakes
The Ask is set in a single Upper West Side living room over one afternoon, following Tanner, a young fundraiser visiting Greta, a longtime donor, to make her case for a significant gift, according to PIX11. Henner plays Greta, described on the production's own site as a longtime donor with strong progressive views, while Purser plays Tanner, the young ACLU fundraiser sent to secure the gift, per theaskplay.com. Purser, an Emmy nominee, is sharing the New York stage with Henner for the first time in her career, PIX11 reports.
The meeting, set in that Upper West Side apartment, erupts into what New York Theatre Guide describes as a battle of wills between the progressive donor and the fundraiser sent to court her. PIX11 characterizes the play as a negotiation over trust, loyalty and being heard, a framing that lines up with the production's broader themes of generational and ideological friction.
Where the Conflict Comes From
Those fault lines run deeper than a simple ask for money. The play portrays generational divisions that emerge even between people who start out sharing the same political ideals, exposing what the production's site calls the cultural and emotional fault lines separating their generations. Concord Theatricals, which licenses the script, notes that the characters must navigate the treacherous power dynamics at the heart of charitable giving.
Part of that friction centers on disagreements over progressive politics and the First Amendment within the American left, with Greta seeing the fundraiser's organization taking positions she views as hostile to free speech, according to a review in TheaterMania. The same review frames the play as an invitation to really hear someone, even if you still walk away disagreeing. Off Off Online reports that playwright Matthew Freeman also uses the conflict as a vehicle to explore the pandemic's toll, folding in social distancing, Zoom calls, masks, isolation and loneliness.
Drawn From Real Fundraising Meetings
Freeman did not invent this dynamic from scratch. He drew on more than 500 of his own meetings as a nonprofit fundraiser while writing the play, according to New York Theatre Guide. Jessi D. Hill is directing the current run, with Adam Cohen producing, per Playbill.
This is not the script's first outing. The Ask premiered at The Wild Project in New York City on September 6, 2024, in a production also directed by Hill but featuring a different cast, Betsy Aidem and Colleen Litchfield, according to Concord Theatricals. The current Theater 555 staging is billed on the show's own site as Matthew Freeman's new play, even as other outlets describe it as a new production built around Henner and Purser following that 2024 premiere.
Tickets and Run Dates
The Ask is running off-Broadway at Theater 555, located at 555 W. 42nd St. in Manhattan, with performances scheduled from October 6 through a limited engagement ending Nov. 22, according to PIX11. Opening night was set for October 13, per Playbill. Tickets, reported to start at $64 when the run was announced, are available through TheAskPlay.com.
