Louise Harrington (Laura Linney), a divorced, thirty-something admission's office at Columbia University's School of Fine Arts is intelligent, pretty, successful, and unfulfilled. That is, until a graduate school application crosses her desk and she arranges to interview the young painter. When F. Scott Feinstadt (Topher Grace) appears, he bears an uncanny resemblance to Louise's high school boyfriend and one true love, an artist who died in a car accident twenty years earlier. Within hours of the interview, Louise and F. Scott have embarked on a passionately uninhibited older woman/younger man affair. But is F. Scott just a reminder of Louise's lost love? And is Scott just trying to wheedle his way into the Ivy League? Adding to the romantic complications is competition from Louise's best friend from high school, Missy (Marcia Gay Harden), who shows upto claim the affections of the boy; Louise's co-dependent ex-husband Peter (Gabriel Byrne); her cynical mother (Lois Smith) and fresh-out of-rehab brother Sammy (Paul Rudd).