Generations Collide in THE ASK — Review

The set-up of Matthew Freeman’s new play is simple: Tanner, a non-binary zillennial, is a Gift Planning Officer at the ACLU, who visits the chic, Upper West Side apartment of Greta, a liberal baby boomer and long-time donor, to solicit her after a year of lapsed giving. What follows is a nuanced and subtle dissection of money, privilege, and division in the progressive Left.

It’s Gen-Z vs. Baby Boomer. Bushwick vs. Upper West Side. 

As Greta, Betsy Aidem (most recently: Prayer for the French Republic, Leopoldstadt) is, at first, a charismatic and breezy host. Conversely, as Tanner, Colleen Litchfield (also in Leopoldstadt) is all nerves and ingratiating professionalism. Tanner is, of course, at work, which precludes them from voicing any of their own opinions wholeheartedly, while Greta gets to enjoy the home court advantage.

Greta believes that the ACLU has strayed too far from its original mission of protecting the Constitution and, specifically, the First Amendment. In her opinion, its bogged down in the culture wars. She sneers at the organization’s emails (“You send too many emails”) about “gender justice” and “canceling student loan debt.” She doesn’t see access to high-speed internet in underserved communities as a Constitutional right, therefore the ACLU shouldn’t be so invested in the fight for it.

While Greta’s complaints are representative of a certain kind of Boomer myopia, Freeman has written a play in which neither character devolves into a stereotype of the generation they represent. Yes, Greta is self-centered and tone deaf—there’s a particularly funny exchange about how hard it can be to own multiple homes—but her grievances are informed by personal struggles and a longstanding history of championing the causes she believes in. Similarly, Tanner’s integrity and capacity for empathy, especially in the face of Greta’s insensitivity, are rooted in their identity.

Jessi D. Hill’s direction is precise and keeps what could be a talk-y play moving at a brisk clip, yet she has given these actors room to breathe, coaxing out two excellent performances in which both actors get to shine. Most importantly, she never misses a chance to bring out the razor sharp comedy in the text.

Aidem is a theatre veteran, whose performance here feels lived in and fully-embodied. Whether she is playing the gracious host or browbeating Tanner over the ACLU’s commitment to “social justice stuff,” she is at ease with the character’s contradictions and emotions. Litchfield is a worthy opponent. Though their performance requires a more understated, buttoned-up quality, Litchfield is adept at letting Tanner’s humanity leak out through their polite business-speak. 

For most of the play, the two characters tiptoe around each other, careful not to cross any lines. It is, after all, a delicate topic. As a Gift Planning Officer, Tanner is not only there to ask about money, but also what might happen once Greta passes away—is the ACLU in her will? Among the many topics Freeman addresses, there’s an interesting conversation going on beneath the surface about ageism and mortality and how we define how much a person is worth.

When the niceties are dropped and the tiptoeing ends, we learn just how personal these fights are to these two people. Without revealing too much, the specter of J.K. Rowling looms large over this piece. As hopeful as Tanner might be, the gap between generations might be too wide to ford. 

In an Author’s Note in the digital program, Freeman writes:

“Although the play draws heavily on my work as a fundraiser at the ACLU, THE ASK is an imagining—a work of fiction…Even the “ACLU” in the play is the subject of dramatic license.”

The Ask deals heavily in realism. The audience gets to watch a thought-provoking and thorny conversation unfold in real time. Realism can be exciting in theatre. However, it doesn’t entirely serve the piece here. While it’s clear from the beginning that Greta has the upper hand, in that she can be as honest as she wants and Tanner must act on behalf of an organization and not as themself, this power dynamic never really shifts. It stagnates the piece, barring it from heading in a more dramatically compelling direction and giving the audience less of a chance to hear from Tanner the person, not Tanner the Gift Planning Officer. 

Still, it’s rare to find theatre nowadays that intelligently explores these themes and remains committed to protecting the humanity of the characters on both sides of the generational divide. 

The Ask runs at The Wild Project through September 28th. For tickets and more information, visit here.