Betsy Aidem and Colleen Litchfield in The Ask. Photo: Kent Meister

While I would love to see The Ask, Matthew Freeman’s tight, achingly precise two-hander, confidently and expertly directed by Jessi D. Hill, follow the path of last season’s Job to ever-bigger venues and longer runs, I’m grateful I got to see it in an intimate space like the Wild Project. Graig Napoliello’s set, a pristine evocation of a moneyed Manhattan apartment with its prestigious art collection and artfully strewn books and bold patterned wallpaper, is a small container floating downstage, bringing you into intense closeup on the faces of the two characters. Hill and the performers pack a remarkable amount of action and momentum into facial microexpressions and the pauses between Freeman’s fast and fluid sentences; for a real-time conversation about charitable donations, the piece often feels surprisingly suspenseful. Tanner (Colleen Litchfield), a twenty-something nonbinary gift planning officer for the ACLU, has been sent to solicit funds from Greta (Betsy Aidem), a wealthy seventy-something photographer and widow who’s a longtime donor. Greta had a solid relationship with Tanner’s predecessor, Carol, which puts Tanner in the tricky position of having to simultaneously do all of the following: build a new relationship, not give away any information on why they’ve replaced Carol, probe gently into why Greta didn’t donate at her usual level last year, supply a boatload of information about the various different methods by which Greta could donate while improving her own tax position, all while building up to make the very specific “ask” of the title.

Freeman has himself worked as a fundraiser for the ACLU, so it’s no surprise that he has a deep and specific understanding of the nuance in such a conversation: every ethical and political and personal minefield that lies beneath the social niceties and in the interstices between sentences. One character is determined to make her point—her “common sense” point with which surely no one could disagree—with a serene aura of reason; the other is tasked with being both a perfect empathetic mirror and the mouthpiece for an institution. Aidem’s Greta is enormously privileged but grievously wounded by the state of the world; her distress and her principles are genuine–but so is her complete inability to understand where Tanner is coming from. Tanner, meanwhile, is essentially professionally forbidden to disagree with Greta; as Freeman says in an interview with The Brooklyn Rail, “Tanner is doing their job…. Greta has freedom to express herself. There’s an illusion that Tanner is an equal person to have an argument with. But that’s actually not the case. Tanner cannot do that, because they need something.” But Tanner has clearly also made the ethical choice not to promise Greta whatever she wants just to get the check signed. Litchfield’s physicality gives away the control required for Tanner to remain studiously neutral; you can almost see the tightrope they’re walking on between their determination to get the win, their frustration with the position they’ve been placed in, and their inability to actually express any real feelings in this context. 

At the heart of the play are deep questions about social justice: On whose behalf are activists working and speaking? How do institutions and societies grapple with generational change and the way social-change goals evolve? (Greta accuses the ACLU of “mission creep,” which can feel like either a fair assessment or a justification for not evolving with the times, depending on where you stand.) Who has the responsibility, the power, and/or the privilege to dictate progressive organizational goals: the people affected, the organizations doing the work, or the donors writing the checks? (Which is not to say there’s no overlap; a small tragedy of The Ask is that Greta and Tanner each fall into two of those categories, and they still can’t find a way to stand in the overlap of their Venn diagram.) At first it seems like Greta just needs a little wooing, but really she wants to be right. It’s not that she wants to be in conflict with Tanner specifically—outside of the unfair impulse to punish them for not being Carol—but that she needs the ACLU’s priorities to match her own and to be validated for that desire. Aidem does a wonderful job keeping us from seeing Greta as simply the bully of the piece; we understand how much she cares but also how easy it is for her to believe that things all work out in the end. And Tanner can spend all day trying to precisely state a position, to explain how disagreement with the ACLU is part and parcel of supporting the ACLU, and still Greta needs to see the thing working out–the way she expects it to.

What’s so clever about Freeman’s script is alongside its bracing clash of ideals and policy priorities mapped onto a generational divide, it’s also quietly dramatizing the issues of access and stakes that Tanner tries–and mostly fails–to explain for Greta. Tanner’s “ask” may be the subject and the inciting incident: the ACLU needs Greta’s money. But some of the play’s most wrenching moments come with what Greta asks of Tanner—because Tanner’s the one who doesn’t get away unscathed if they say no. All of Greta’s passion is real, her commitments and ideals deep, her experiences valid. It’s just that she can’t lose this game; you can agree with Greta and still see how she’s putting her thumb on the scale.

I mentioned Job, above, and there is something valid about the comparison beyond one’s hopes for an afterlife for The Ask. The dynamics are on the surface similar–the younger participant in this high-stakes conversation needs an explicit, theoretically attainable thing from the other to hold on to a precarious job; the tension grows over the course of the 90 minutes. But where Job slips ever further into a facile sensationalism, The Ask stays firmly grounded in its here and now–and nonetheless, I feel like its stakes end up higher.