
For non-profit fundraisers, it’s rarely a straight line to the money. For Tanner (Colleen Litchfield), it’s practically a trek up a mountain laced with landmines. They are half of the cast in Matthew Freeman’s The Ask, a two-hander that lifts the lid on philanthropic giving and the issues it presents when big checks are on the line.
The cast’s other half, Greta (recent Tony nominee Betsy Aidem) is an affluent, liberal, older New Yorker. She has invited Tanner into her apartment that’s she had forever and “could never give up this location.” Bushwick based theater major- turned- fundraiser Tanner has traveled to Greta’s place with one goal in mind: A $500,000 donation to their organization, the ACLU.
In 80 minutes, the two have a subtle debate covering personal values, the mission of the ACLU, the clinical definition of pregnancy—and why Tanner isn’t Carol. Due to recent layoffs- or as the ACLU President pitifully phrased it- “right sizing”, Carol was laid off, leaving Greta in the lurch. “It makes me feel like your predecessor was treating me a certain way because it was her job and when it was no longer her job, she didn’t feel obligated to show me any grace or politeness,” Greta explains. “That makes me feel distrustful, if that’s the right word.” After an awkward start, the conversation becomes increasingly more uncomfortable but compelling to watch.
The old adage, “write what you know” was taken to heart by playwright Freeman, who spent several years as a fundraiser for the ACLU. It’s clear that he is a master on the subject but he has cautiously avoided creating a work that is too “inside baseball.” Instead, he’s given us material that is both specific and universal. His characters are well-rounded and avoid the usual stereotypes that could easily-and lazily been portrayed. Instead, we’re introduced to two well-meaning individuals with big generational gaps who are wrestling with their own convictions. Who is the protagonist? Who is the antagonist? Freeman wisely never makes a distinction and at times. Greta and Tanner are both. Yet he leaves the ultimate judgement in our hands.

Aidem and Litchfield are first rate actors who make this piece crackle, thanks to Jessi D. Hill’s sharp and precise direction.
The Ask is a well-crafted, thoughtful and wise piece of theater that will undoubtedly appeal to anyone concerned not only about philanthropy, but about the state of the world. Perhaps Freeman will someday craft a play that delves into how philanthropic wealth only further drives the inequality gap and serves exclusively as a tax haven for the lucky few. Until then, we’re fortunate to have The Ask.
The Ask is now playing through September 28th at the wild project 195 E. 3rd Street between Avenues A & B. New York. For tickets and info, click here .
