“Taut. Timely. Telling.” — TheaterMania
The Ask
A new play by Matthew Freeman
Off Broadway 2026
What happens when two people on the same side of the political spectrum can’t find common ground?
This psychologically-complex battle of wits pits a sophisticated donor, Greta, against Tanner—a young, nonbinary representative from the American Civil Liberties Union tasked with soliciting Greta’s continued patronage.
In Greta’s Upper West Side apartment they dodge and parry, armed with viewpoints forged in different times and spaces—revealing the gaping chasm between them.
Matthew Freeman | Playwright
Matthew Freeman is a Brooklyn-based playwright. He was a MacDowell Colony Fellow and is a New Dramatists alum, where he proudly received the Joe A. Callaway Award. He has received support from the Venturous Theater Fund and was awarded the 2021 Kesselring Prize. Freeman is a graduate of Emerson College.
He has been produced at The Brick Theater, HERE Arts Center, House of Yes, FPAC/The Assemblage in Boston, St. Mark's Church, Dixon Place, Access Theater, East 4th Street Theater, The Metropolitan Playhouse, Manhattan Theatre Source, The New Ohio, and 80WSE Gallery.
His plays and monologues have been published by Samuel French, Applause, Smith & Kraus, NYTE, and Playscripts. Plays include The Ask, Silver Spring, The Sea The Mountains The Forest the City The Plain, The Conversation, A Long Trip By Sea, The Hollow, That Which Isn't, The Language, Bluebeard, When is a Clock, The Listeners (Nominee: Best Production - Performance Art: New York Innovative Theatre Awards 2015), Why We Left Brooklyn, The Starving Dress, The Most Wonderful Love, Glee Club, The Death of King Arthur, Confess Your Bubble, Cloud Cuckooland (with Djahari Clark) and Brandywine Distillery Fire.
His audio pieces, with David Greenspan, Jessi D. Hill, Moira Stone and many others, have been a part of the HearNow Festival, New Dramatists Active Listening, Atlanta Fringe Radio, and released as podcasts by Theater Accident.
As a director, Freeman staged and co-wrote Steve Burns Alive at Howland Culutral Center; his evening of short plays The Hollow (Brick Theater);The Zebra Shirt of Lonely Children by Matthew Trumbull at the NY International Fringe Festival (Encore Series; Award, Overall Excellence in Solo Performance) and the Minnesota Fringe Festival; and his own adaptation of the mystery plays, Genesis, with Handcart Ensemble.
He lives in Brooklyn, NY with his wife, magical author Pam Grossman.
Jessi D. Hill | Director
JESSI D. HILL is a theatre director based in New York City. Latest NYC credits include Off-Broadway productions of Crystal Skillman’s OPEN (NY Times Critic’s Pick), Robert Montano’s SMALL (2024 Drama Desk and Outer Critics Circle Nominations), Matthew Freeman’s THE ASK (2025 Drama Desk Award Nomination), Chisa Hutchinson’s SURELY GOODNESS AND MERCY, Larissa FastHorse’s VANISHING POINT, and Cusi Cram’s THE HELPERS. NYC credits include new work at New York Theatre Workshop, The Public Theater/Joe’s Pub, The Playwrights’ Center, Primary Stages, Labyrinth, The Women’s Project, 59E59, P73, Cubbed Thumb, LaMama, The New Group, Rattlestick, Ensemble Studio Theatre, terraNOVA Collective, Culture Project, Musical Theatre Factory, The Acting Company, The Barrow Group, PS122, Abingdon, Baruch Performing Arts Center, New Dramatists, The Playwrights Realm, New Georges, Naked Angels, The Wild Project, and others. Recent Regional Credits: Old Globe, George St. Playhouse, A.R.T, People’s Light, Diversionary, Contemporary American Theatre Festival, TheatreSquared, Orlando Shakes and others.
She has been a director and teacher in professional training programs at Yale School of Drama, Juilliard, Eugene O’Neill Theatre Center/NTI, Fordham University, Powerhouse/NY Stage & Film, NYU/Tisch, Strasberg, The Atlantic School, Playwrights Horizons, and others.
Jessi is a recipient of the Denham Fellowship from the Stage Directors and Choreographers Foundation, an Alum of the Women’s Project Lab, and an Affiliated Artist at New Georges. Her work has been seen internationally in Edinburgh, London, New Zealand, Berlin and Hamburg, Brussels, Ukraine and Rome. MFA: Yale. Member SDC.
Adam Cohen | Producer
A tone-deaf theater kid, Adam worked in education, publishing and technology marketing. Post-pandemic, he interned for a Tony-Winning producer assisting on her off-Broadway show for investor management and helping find investors for Tony-winner Parade. He served as Managing Director for Mile Square Theatre in Hoboken, NJ. and Development Associate at Parsons Dance. He is a graduate of Bennington College, and Brooklyn College’s MFA in performing arts management program.
Broadway Co-Producer:
Sunset Boulevard (2025 Tony for Best Musical Revival), Gypsy (2025 Drama Desk Outstanding Musical Revival), Operation Mincemeat, John Proctor is the Villain, Suffs, and Fat Ham. As an investor, he’s been part of work as diverse as Kimberly Akimbo, Purpose, and Merrily We Roll Along.
Jessica R. Jenen / JRJ Theatrical | Executive Producer / General Manager
Ms. Jenen is a four-time Tony Award winning Broadway producer, and has been an international producer and theatrical manager for over thirty years. She is a proud member of the Board of Directors of the Broadway Producer’s Alliance, an organization dedicated to promoting collaboration, innovation, and communication within the Broadway producing community. Executive Producer, 2024 & 2025 Drama Desk Awards at NYU Skirball. 2024 featured Co-Hosts Sutton Foster & Aaron Tveit. The 2025 Awards Benefitted the Entertainment Community Fund and featured Co-Hosts Debra Messing & Tituss Burgess. 2024-25 Broadway season: Sunset Boulevard (Tony Award); All In: Play About Love; The Last Five Years; Buena Vista Social Club, Dead Outlaw. Previous Broadway credits: Stereophonic (Tony winner for Best Play, the most Tony nominated Play of all time, with 13).Tony nominated Gutenberg The Musical, which completed its profitable record-breaking run, starring Josh Gad and Andrew Rannells; The Who’s Tommy (Tony nomination); Previous: Parade (Tony Award), Company (Tony Award); An Evening with Patti Lupone and Mandy Patinkin; Venus in Fur (Tony nomination), which was the most produced new play in America during the 2014 season. Additional Broadway credits: Into the Woods(Tony nomination), Life of Pi, winner of 5 Olivier Awards in London’s West End; New York, New York. National Tour: Into the Woods. As Executive Producer of THE BROADWAY COMPANY with producer Jon B. Platt: I’ll Eat You Last, The Heiress, Cat on a Hot Tin Roof, Death of a Salesman, Clybourne Park, and Nice Work If You Can Get It. In 2013 she formed JRJ Productions LLC, continuing to pursue commercial endeavors and functioning as Executive Producer, Executive Consultant and General Manager for commercial projects and not-for-profit theatrical institutions.
West End: A lead producer of the Olivier Award winning Get Up, Stand Up: The Bob Marley Musical, which completed its long run at the Lyric Theatre, West End, London. 2024-25 West End Productions: Giant, Stereophonic, Fiddler on the Roof, Evita. JRJ Productions is also proud backer of the following West End productions: The Fifth Step, How to Fight Loneliness; Sunset Boulevard; Stranger Things: The First Shadow; A Little Life; Dr. Semmelweis; The Motive and the Cue; Patriots; A Streetcar Named Desire; Standing at the Sky’s Edge; The Shape of Things; Strange Loop; The Ocean at the End of the Lane; Accidental Death of an Anarchist; The Crucible, and the recent sold out Macbeth starring David Tennant and Cush Jumbo.
