Plot

A car magnate watches his personal and professional life hit the skids because of his business and romantic indiscretions.

Ben Kalman is aging: he has heart problems, his marriage is over, he's lost a fortune after being caught cutting corners in his East Coast car business, and he's sleeping with as many women as possible - the younger the better. He's chosen his current girlfriend, Jordan, because her father can help him get a new auto dealership; she's asked him to escort her daughter, Allyson, 18, on a visit to a Boston college campus. He behaves badly, and there are consequences to his love life, his finances, and his relationship with his daughter and grandson. Is there anywhere he can turn?—<jhailey@hotmail.com>

The film opens with 54-year-old Ben Kalmen (Michael Douglas), an attractive and very successful car dealer in the New York area, at his annual medical check-up; his doctor tells him he needs a CAT scan to get a better look at his heart, due to an 'irregularity' in his EKG.

About six years later, Ben's fortunes have drastically changed. He is taking oral medications, but he never got the prescribed heart tests, and his lost sense of 'immortality' sent him off on a self-destructive binge: habitual lying, sexual affairs, divorce, and bad business decisions that almost put him in prison. He is broke, borrowing money from his daughter Susan (Jenna Fischer), and still unwilling to accept his age, ignoring his heart problem, and has a serial sexual appetite.

Ben, who cheated often on his wife Nancy Kalmen (Susan Sarandon), accompanies the 18-year-old daughter of his girlfriend, Jordan Karsch (Mary-Louise Parker), to her college interview. Ben is an alumnus of the university and was even a building donor during his more prosperous days. Ben meets an impressionable student named Daniel (Jesse Eisenberg) on campus who appreciates his wisdom and advice. Ben talks himself into bed with Jordan's daughter, Allyson (Imogen Poots).

He expresses desire to continue the relationship, which Allyson dismisses as a one-time experiment with an older man, and crossing 'the Daddy' fantasy experience off her 'list'. Frustrated with Ben, Allyson flippantly tells her mother about the sexual encounter. Jordan breaks off contact with Ben and withdraws the support Ben needs to open a new auto dealership. While discussing his past due rent with his building manager (Lenny Venito), his daughter Susan appears and tells him he is no longer welcome in her family's life because of his inconsistency and unreliability as grandfather of her son, after discovering an affair Ben has had with the mother of one of her son's friends.

Facing eviction, Ben asks his college friend Jimmy Marino (Danny DeVito) to give him a job at his diner on campus. Allyson is upset to find Ben working near her college campus and informs her mother. He receives a call from Jordan, demanding that he move out of college town immediately. If he does not, Jordan tells Ben, she will have her ex-husband's contacts physically persuade him to do so.

At a college party cruising, after hitting on one girl he recognizes as a customer from the diner to no success, and unable to help himself, Ben makes a sexual advance toward Daniel's new girlfriend, Maureen (Olivia Thirlby). Shortly after the girl rebuffs him, he is severely beaten by an ex-police officer (Arthur J. Nascarella) whom Jordan's ex-husband sent to the campus. After discussing his view of life with Jimmy, he collapses and is put in hospital. After a few days recovering, Susan checks on him to his surprise and happiness at their 'reconciliation'. But he leaves the hospital against advice. He seeks out and apologizes to Daniel for his indiscretion. He then finds Nancy on the bench where they met. She has found out about his medical condition.

He tells her why he went 'off the rails': aging, and the prospect of dying, made him start to feel 'invisible', so he decided to plunge into life with full gusto. She tells him that's no excuse, but she understands and offers to give him a ride back to New York city. The film ends with Nancy waiting in the car for his decision and a young woman walking by Ben, still sitting on the bench, in the opposite direction. Ben looks one way at Nancy, then the other way at the woman. He stands and looks into the camera. Which way he should he go?