As Amy Minsky faces the oppressive weight of her impending divorce from her husband David, an entertainment lawyer, she retreats to her childhood home in Westport, Connecticut. Once a spirited thirty-something, Amy now finds herself trapped in a fog of lethargy, spending her days immersed in classic comedies, especially those featuring the Marx Brothers. However, her mother, Ruth, persistently nudges her back into the world, insisting she attend a dinner party for friends Gwen and Larry Hammer. Meanwhile, Stan, Amy's father and a lawyer with his own aspirations, hopes to win Larry as a client, which would allow him to realize his dream of traveling the world with Ruth.
During the dinner, tension builds when the topic of Amy’s stalled career arises, revealing her abandonment of a master’s degree in photography to marry David. Things spiral further when Ruth makes a casual comment about Amy's childhood weight, pushing her to seek refuge in the home’s new addition. It is here that Jeremy Hammer, Larry's 19-year-old son and a burgeoning actor, finds her, leading to a fervent kiss that sparks an unexpected and secretive affair between them, creating a web of deception due to their respective familial ties and the age difference.
As this covert romance unfolds, Amy slowly begins to rediscover her self-esteem. In a twist, Jeremy’s mother, Gwen, mistakenly interprets the relationship as a sign of her son's supposed homosexuality, a theory he willingly supports. As their bond deepens, Jeremy starts questioning his acting career, which he feels pressured into pursuing only to appease his mother, navigating the complexities of ambition and affection.
However, challenges arise when Amy rebuffs Jeremy's idealistic visions of their future together, prioritizing her father's retirement plans over her own desires. This leads her to reluctantly agree to a lackluster date with Phil, a recently divorced man, which starkly highlights her emotional discontent.
In a pivotal moment, Amy heads to New York City for a crucial meeting with David to finalize their divorce. The emotional weight of their breakup becomes clear, as David's smug justifications for their marriage's collapse shock Amy into a newfound resolve. She demands a fair divorce settlement, grateful for the opportunity to escape the clutches of their unfulfilling union.
The family's reunion to celebrate Stan's business success is marred by tension, with Jeremy still reeling from a previous argument with Amy. When Amy takes the initiative to apologize, their heartfelt moment on the couch is abruptly interrupted by the arrival of their parents.
As events unfold, Ruth faces the disappointment of Stan's choice not to retire, revealing his struggle with stepping away from his career. Amy reassures him about their travel plans, announcing her intent to eventually leave the family home for a place of her own.
In a bittersweet farewell, Amy visits Jeremy before he starts his journey to Oberlin College. They agree to remain friends, highlighted by Amy’s revelation of her plans to complete her Master’s thesis and travel around the world with her mother. As Amy drives away in a taxi, she feels rejuvenated and unburdened by her past, allowing the film to conclude on a note of hope and new beginnings.
