In 1986, In Brooklyn, New York, the dysfunctional family of pseudo intellectuals composed by the university professor Bernard and the prominent writer Joan split. Bernard is a selfish, cheap and jealous decadent writer that rationalizes every attitude in his family and life and does not accept "philistines" - people that do not read books or watch movies, while the unfaithful Joan is growing as a writer and has no problems with "philistines". Their sons, the teenager Walt and the boy Frank, feel the separation and take side: Walt stays with Bernard, and Frank with Joan, and both are affected with abnormal behaviors. Frank drinks booze and smears with sperm the books in the library and a locker in the dress room of his school. The messed-up and insecure Walt uses Roger Water's song "Hey You" in a festival as if it was of his own, and breaks with his girlfriend Sophie. Meanwhile Joan has an affair with Frank's tennis teacher Ivan and Bernard with his student Lili.
It's the mid 1980's. Bernard and Joan Berkman and their two sons, mid-teen Walt Berkman and adolescent Frank Berkman, are a liberal minded family living in Brooklyn. Bernard is an opinionated, condescending and competitive man who works as an English professor. His past glories as a published writer have given way to teaching, but not without a fight. Joan, who didn't start writing until after they got married, has had more recent writing acclaim, her writing success which is one of the many strains in their marriage, which led to Joan having past indiscretions. As such, they announce to Walt and Frank that they are separating after seventeen years of marriage, that Bernard has taken another apartment five subway stops away, and that Bernard and Joan will have joint and equal time custody of the two boys. The boys don't much like this situation, not so much because of their parent's break-up, but because they more closely resemble and thus associate with one parent, and would rather live with that parent to the exclusion of the other: Walt with Bernard, and Frank with Joan. In addition to and in part because of the upheaval in the boys' lives, the boys are facing their own issues. Walt plagiarizes some material - in his mind, that work being something he would have been able to write - and pushes away his girlfriend Sophie solely because he thinks he can do better. Frank is testing his sexual being, leaving a bit of his manhood in public locations. All the while, the boys have to maintain their relationships with both parents, who themselves are embarking on new relationships, Bernard with one of students named Lili, and Joan with Frank's tennis coach Ivan.
The patriarch (Jeff Daniels) of an eccentric Brooklyn family claims to once have been a great novelist, but he has settled into a teaching job. When his wife (Laura Linney) discovers a writing talent of her own, jealousy divides the family, leaving two teenage sons to forge new relationships with their parents. Linney's character begins dating her younger son's tennis coach. Meanwhile, Daniels' character has an affair with the student his older son is pursuing.