A down-on-his-luck real estate agent grows increasingly despondent as his life spirals down a rabbit hole of unexpected disappointments, forcing his sister to throw an unorthodox 50th birthday party in a desperate attempt to show him the true impact his life has had on the world and prevent him from committing the unthinkable.

SYNOPSIS:

For Charles Who Will Die Someday is a dark dramedy that explores grief, denial, addiction, and the fragile threads of family through the unraveling life of Charles McKay.

The story follows Charles, a nearly 50-year-old recovering alcoholic whose life is quietly collapsing. Once married and stable, he is now separated from his manipulative wife Raina, secretly homeless, and scraping by as a failing real estate agent. He drifts between empty houses he illegally “housesits,” clinging to routines—like his anthropomorphized coffee maker—that give him a false sense of stability. His humor and charm mask a deep avoidance of reality, as he refuses to fully confront his financial ruin, his broken marriage, and his emotional isolation.

The narrative is anchored by Charles’s strained but deeply bonded relationship with his sister Ellie, who is herself drowning in grief and hardship. A widow whose husband died suddenly and whose son Ian was killed in a hit-and-run, Ellie struggles to raise her troubled younger son Hunter while reentering the workforce after years away. Her life is chaotic and raw, filled with financial stress, anger, and unresolved trauma. Despite this, she serves as both Charles’s moral compass and emotional lifeline—though their relationship becomes increasingly strained as Charles withholds the truth about his situation and continues entangling himself with Raina.

Raina represents both temptation and toxicity. Charismatic yet manipulative, she maintains control over Charles even after their separation, drawing him back into a cycle of emotional dependency and dysfunction. Their relationship is further poisoned by the revelation that she had an affair with Ellie’s late husband Gavin—an explosive secret that underscores the story’s themes of betrayal and suppressed truth.

The family dynamic is further complicated by their mother Deirdre and her recently deceased husband Ray, a crude and often offensive figure whose death forces the characters into yet another confrontation with mortality. The film repeatedly juxtaposes absurdity with tragedy—moments of biting humor, surreal imagery, and social discomfort collide with raw depictions of grief, addiction, and existential despair. Charles’s recurring dream of failing to save Ian encapsulates his deep guilt and helplessness in the face of loss.

As Charles spirals—losing potential clients, alienating his family, and facing mounting financial pressure—he is pushed toward a breaking point. His reluctant return to Alcoholics Anonymous meetings highlights the central tension of the story: staying sober is not enough when life itself feels unmanageable. Ultimately, the screenplay paints a portrait of a man suspended between avoidance and accountability, surrounded by people who are equally damaged but still fighting to survive.

Blending dark comedy with emotional realism, the story examines how people cope with death, failure, and the passage of time—suggesting that growth requires not just endurance, but the courage to face painful truths and reconnect with others before it’s too late

FOR CHARLES, WHO WILL DIE SOMEDAY