The film begins with Ben Kalmen, portrayed by Michael Douglas, a 54-year-old car dealer who is not only attractive but also successful in the competitive landscape of New York. During his regular medical check-up, his doctor advises him to undergo a CAT scan due to an abnormality observed in his EKG, hinting at underlying heart concerns. Fast forward to six years later, and Ben's life has taken a significant downturn. He finds himself relying on medications and grappling with the consequences of neglecting his health. This denial of his mortality has spiraled him into a cycle of self-destruction that includes deceit, extramarital affairs, a divorce, and reckless business decisions that have nearly led him to prison.
Financially unstable, Ben is forced to borrow money from his daughter Susan, played by Jenna Fischer, while simultaneously refusing to come to terms with aging and his medical issues. His hedonistic lifestyle continues to flourish despite his failing heart. Adding to the complications, Ben is entangled in an affair with Nancy Kalmen, his estranged wife, a role brought to life by Susan Sarandon. Accompanying the daughter of his current girlfriend, Jordan Karsch, Ben makes his way to a college campus where he once thrived as an alumnus and benefactor.
While on campus, he crosses paths with a young and impressionable student, Daniel, played by Jesse Eisenberg, who is drawn to Ben's seemingly profound insights. In an unexpected twist, Ben becomes involved with Jordan's daughter, Allyson, portrayed by Imogen Poots. Despite their rendezvous, Allyson treats the encounter as a mere fling, one that fulfills her curiosity about older men before moving on. This leads to tensions with Jordan, who upon being informed, severs ties, impacting Ben's efforts to establish a new auto dealership.
As Ben faces eviction, he seeks employment at a diner owned by his college friend, Jimmy Marino, played by Danny DeVito. Encountering Allyson again makes the situation worse, leading Jordan to demand his immediate departure from the college town under threat of force from her ex-husband. After a disastrous attempt to flirt at a college party, Ben finds himself battered by an enforcer sent by Jordan's husband.
A turn of events finds Ben hospitalized after collapsing, prompting a reconciliation with his daughter, Susan. However, defying medical advice, he leaves the hospital early. In a moment of humility, Ben seeks out Daniel to apologize for his inappropriate behavior, and later attempts to reconnect with Nancy on a bench where their relationship once blossomed. In a candid conversation, he confesses that the anxiety surrounding aging and potential death has driven him to live recklessly and chase thrills. Although Nancy acknowledges his struggle, she does not excuse his actions, but still offers him a ride back to the city.
The film comes to a poignant close with Nancy waiting in the car for Ben's decision while a young woman passes by him in the opposite direction. He finds himself at a crossroads, contemplating between returning to Nancy or pursuing the fleeting moment with the young woman, ultimately leaving the audience wondering about his choice as he gazes into the camera.
