Ben Kalman is approaching 60. He has health problems, he is divorced and he has lost a lot of money doing shady deals with his former business, car dealerships. Now he is dating a woman, Jordan, because of her father's business connections. As a favor to his girlfriend, he escorts her daughter Allyson to a college interview as he happens to know the dean. There, he hangs out with Daniel Cheston, who gives them a tour of the campus. Cheston is an insecure freshman who got dumped by his girlfriend. Ben gives him some dating advice and later in the film, when Ben goes back to the campus to get work from an old friend, the two meet again. Cheston is now dating Maureen, a student in his Spanish class.

Here we are at a party. Ben is drinking and has just been rejected by a girl. Maureen walks up to him and Ben hits on her, promising not to tell Cheston if the two sleep together. Maureen scolds him for trying that and tells him that she is happy with Cheston...