The Ask

by Matthew Freeman

When Tanner, a young activist and fundraiser from the ACLU, solicits Greta, an affluent donor on the Upper West Side of Manhattan, the seams between two generations of progressives start to show.

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The Ask

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Brian Olsen: The Ask by Matthew Freeman

“

I was fortunate enough to see the original production in New York in 2024, and I still think about it (and rave about it). A brilliant examination of wealth and status on the left, and the power differentials that come with them. A fantastic showcase for two actors.

I was fortunate enough to see the original production in New York in 2024, and I still think about it (and rave about it). A brilliant examination of wealth and status on the left, and the power differentials that come with them. A fantastic showcase for two actors.

”
Arlene Hutton: The Ask by Matthew Freeman

“

A stunning achievement, a brilliant two-hander: a conversation and a negotiation that is so relevant today. The characters are well drawn and the dialogue sparkles. This play should be performed all over the country, but will theaters be brave enough to produce it?

A stunning achievement, a brilliant two-hander: a conversation and a negotiation that is so relevant today. The characters are well drawn and the dialogue sparkles. This play should be performed all over the country, but will theaters be brave enough to produce it?

”

GRETA – A white woman in her early 70s. A liberal feminist who financially supports the causes we all care about.

TANNER – Late 20s. TANNER presents as gender non-conforming. TANNER is a Gift Planning Officer at the American Civil Liberties Union.

Production History

Type Professional, Organization Theater Accident, Year 2024

Awards

Nomination - Best Actor (Betsy Aidem)

Drama Desk

Finalist

2025