THE MORE LOVING ONE

On a storm-lashed night on Long Island, Jamie Brenner — a meticulous tax attorney known for his restraint — waits for Liv, a sharp, self-possessed graduate student who supplements her income through sex work. Liv’s skills are tested when her assignment becomes keeping a grieving widower company.

What unfolds is less a transaction than a reckoning. As wine and argument erode their defenses, questions of class, power, and emotional labor give way to something more dangerous. Hovering at the edges of the evening is Jamie’s wife, Sid — whether as memory, conscience, or living presence is unclear — a woman whose love has placed him under an unthinkable obligation.

As the night deepens, Jamie must confront a question he has tried to rationalize: when the person you love most asks something irreversible of you, is fulfilling that request an act of devotion — or an abdication of responsibility?

By dawn, three figures are locked in a shifting triangle of desire, loyalty, and obligation, circling a single unsettling question: what does it mean to be the more loving one?

SAMPLE

CAST OF CHARACTERS

JAMIE BRENNER
Late-30s. A disciplined tax attorney whose life is built on logic, restraint, and the careful management of risk. Jamie believes in order — financial, emotional, moral. But love has undone his calculus. Beneath his civility lies a man wrestling with a private and unthinkable obligation, one that threatens his identity as a husband and a moral being. He is intelligent, self-aware, and adept at rationalization. Whether he is courageous or cowardly depends on the answer to a single question: Is he the more loving one?

SID BRENNER
Late 30s. Jamie’s wife. Wry, incisive, and emotionally exacting, Sid possesses both intellectual rigor and sexual ferocity fueled by deep childhood wounds. She is neither saint nor victim; she refuses sentimentality and demands honesty — especially from Jamie. Whether she appears as memory, conscience, projection, or presence, she’s the emotional fulcrum of the play. For Sid, love is measured not in words but in action, and her demand is simple, devastating, and absolute.

LIV
Mid-20s. A graduate student who supplements her income through sex work. Quick-witted, pragmatic, and perceptive, Liv has learned to read men with professional efficiency. She enters the evening expecting a familiar transaction but finds herself in unfamiliar terrain, keeping a grieving widow company. Though she trades in intimacy, she guards her own carefully. Liv’s clarity and refusal to be patronized destabilize Jamie’s assumptions about power, class, and emotional labor. Over the course of the night, Liv becomes more than a hired companion; she becomes the unlikely ally who helps Jamie find the clarity and resolve to meet love’s demand.

ALLY
Mid-20s. Jamie’s legal assistant. Played by the actor who plays LIV.