Season synopsis
Contains spoilers for this season and earlier seasons.
Alan, Jake and Charlie settle into the shared Malibu routine, but Alan is still struggling with the financial and emotional fallout of his divorce. He hopes Judith will move on with a new partner and reduce his alimony, while Jake's school problems and ordinary growing-up needs keep pulling both brothers into parenting. Charlie continues dating without much commitment, although old girlfriends return and Rose's growing closeness with Alan gives the brothers a new reason to compete and tease each other. He also attempts to push Judith toward remarriage after Charlie points out the possible alimony change, but Alan's eagerness creates more awkwardness than progress. His desire to have Jake's mother move on often says as much about his own finances as his concern for her.
Evelyn's demands repeatedly bring her sons back into her social orbit, and the brothers discover that their ideas about her dating life are complicated by their childhood. Jake's account of a weekend with the family becomes the focus of the finale: his classroom report reveals that Charlie unknowingly slept with Natalie, the much younger wife of Norman, an older man. Norman confronts Charlie, then recognizes something of himself in the younger man. When Evelyn arrives, the two hit it off; she sends the family and Berta to a movie, and they return to find her with Norman. The season closes with Evelyn pursuing a new relationship and the brothers surprised by the turn.