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?
Ben Kalmen (Michael Douglas) is a successful car salesman who is getting his annual physical. His doctor tells him that his EKG indicates he may have heart problems, and is ordering further tests.Six-and-a-half years later, Ben walks through New York City to meet his daughter Susan and her son at a park, and he cant help but notice an attractive young woman. He chafes at being called Granddad and is quite self-conscious about being older, since he is nearly 60. They go on to meet with his ex-wife for lunch, where again Ben spies another attractive younger woman.Ben goes to visit his wealthy girlfriend Jordan, whom he admits is advantageous to him because her father should be able to help him regain his place within the car dealing community. As we learn, in recent years Ben became involved in serious financial scandals that torpedoed his professional reputation, and he is now trying to use Jordan's influence to secure a property for a new dealership. At the moment, Ben has agreed to take Jordans explicitly 18-year-old daughter Allyson up to Boston to visit the college he attended as a young man. Ben is not only an alumnus, but was once so rich that his donations motivated the school to name the library in his honor, so Jordan assumes he will ensure Allysons admission to the school.On the trip, Ben asks Allyson about her penchant for drinking at a young age, and she counters by pointing out that he cheats on her mother. They agree to not badger each other and to enjoy the weekend on their own terms.Once they arrive on campus, Ben quickly confronts an arrogant student who insults him, resulting in fisticuffs between them. Campus security intervenes, confirming that Allyson is indeed 18, and warning Ben to stay out of trouble, even if he is a notable alumnus. Ben meets Daniel, a student assigned to be his guide, while Allyson goes on a tour with a lacrosse player. Ben goes back to Daniels dorm and makes a quick read of him as a romantic loser. Telling Daniel that he needs to seize his opportunities, Ben proceeds to chat up two girls in the hall and gets himself invited to a party, where he tells Daniel that he too was an awkward, working-class kid in college. He says all that changed when he had a crush on a girl and then found out another guy seduced her before him. After his initial shock, Ben learned from the guy that she enjoyed wholly strenuous coitus, and that gave him the confidence to pursue her so that he was soon enjoying rough sex with her.Ben goes back to his hotel where he sees Allyson at the bar being regaled by the lacrosse player. Ben pulls Allyson aside and tells her she stands to gain little from the sexual transaction that is about to happen. After dumping the player then, Allyson continues talking to Ben about how shes had a lot of sex since she was 14, but none of it has been so great. Ben advises her that she needs to take more control of a guy when she has sex, and show her partner what she wants. Allyson asks Ben how he likes sex with her mother, and he coolly responds that she can at least get him off. Exceedingly soon thereafter, Ben is asking Allyson to show him what she wants as they make love in their hotel room.Ben calls Allyson the next morning from bed. She is already on her way back to New York, but says she had fun with Ben and that everything is copacetic. They both agree to not tell Jordan they had sex.Back in New York, Ben gets the good news that his new dealership will be approved, and he joins Jordan to celebrate, along with Allyson, who has somehow already been accepted to the college. Ben joins the two at Jordans swank apartment, only he is chagrined that Allyson shows little interest in spending any more time with him. Away from Jordans earshot, Allyson thanks Ben for helping her over the Daddy thing and says that she used his advice on the next guy she had sex with, whom she was able to mount with assurance and really enjoy the intercourse. For no apparent reason, then Allyson blurts out to Jordan that they had sex while visiting Boston, and walks away.Ben goes to his daughter to explain his pathetic situation. Susans husband walks in the room, objecting to how Ben has lived his life and had such a negative influence on her. Ben comments to Susan that he tried to shield her from the bad aspects of his past, and then slyly asks her if she can loan him money.After learning that the supposedly secure new dealership has fallen through, Ben meets with his private banker, who informs him that his bank needs to release him as a client, given that they can no longer ignore his corruption and losses. Ben becomes irate, yet manages to bring home a woman he vaguely knows, because she is Susans friend. After their night together, the woman asks Ben about his health, and he tells her he has not been back to a doctor in over six years.As a result of sleeping in with this latest conquest, Ben misses his grandsons birthday party. He thereafter brings a cake to Susans house and plays video games with his grandson, but once again asks her for money, making her indignant. He even goes to visit his ex-wife and asks her for money; while they are amicable and she has become quite successful in real estate, she does not support him. As Ben learns from an associate, he has really managed to turn all his friends into enemies.Ben packs up his nice digs and moves to a humbling apartment, where he is unable to pay the rent for two months. Susan shows up, infuriated with him after learning that he not only slept with her friend but has since been ignoring her. When she asks him to seek professional help for all the trouble hes put himself through, he refuses, and she then refuses to see him again.Ben returns to the college town where he took Allyson, because he still has one friend there, a college buddy named Jimmy who now owns a greasy spoon that is popular with local students. Ben asks Jimmy to give him a job, and he agrees. Ben soon wonders why Jimmy does not chase after the college girls, and the old friend explains that after graduation, the girls are not so attractive anymore. Besides, he has a wife at home with whom he is happy.Allyson happens to come by the diner one day and is suspicious that Ben has followed her. He explains that he is not chasing her but simply trying to get back on his feet. Jordan soon calls Ben and tells him that he must leave town because he is a nuisance to her daughter, and she threatens that her father will do even more damage to him.Daniel invites Ben to a party, where the elder ruminates about his sad situation with Allyson and tries to commiserate about women. Ben later asks Daniels girlfriend what she is getting out of that transaction, and she abruptly shuts him down, recognizing that he is coming on to her, asking if he is not too old for such behavior. She says he is not like Daniel smart, sweet, and funny but Ben counters that in fact he once was, only it did not last.On the way home from the party, the drunk Ben is accosted by a thug who beats him and orders him to leave town the next day, saying that Jordans father sent him. Jimmy tries to console Ben, who bemoans how much he has lost in his life due to his misguided transgressions, and then collapses. Ben wakes up in a hospital with Susan by his side, and apologizes for how he treated her friend. Later, a nurse tries to tell him he has a bad heart, but he insists on leaving against medical advice.Ben stops by Daniels building and they awkwardly acknowledge that Ben was lecherous with his girlfriend. Ben tells Daniel to hold on to her if she is good for him.Ben comes across his ex-wife as he walks back across campus, sitting on the bench where they first met in their youth. She asks about his heart tests, and he confesses that on the day he first had trouble over six years earlier, he immediately went out and cheated on her with some random woman he met. He explains that he had been feeling like such a success in life and business up to that time, doing television ads and touting himself as so honest, and after that first affair, he just kept cheating, on his marriage and his finances, because he did not want to deal with the compromises of facing death. He never expected to grow old, he never wanted to become invisible.With sincere concern, Bens ex-wife tells him she can drive him back to New York City. She walks off to her car, leaving him sitting on the bench. He looks over at her, and just then a college girl walks in front of him in the opposite direction. Ben stands up, looking forward, needing to decide which way to go.