Charlie gets tired of Alan's mooching and reaches the breaking point during the brothers' double date. Jake is left home alone for the first time.
Alan suffers from insomnia. He visits his psychiatrist, who reveals that the cause of Alan's sleepless nights is his jealousy towards Charlie, and his inability to glide through life.
Berta's daughter, Naomi is pregnant and Berta drags Charlie with her when she confronts the baby’s father. Alan reveals a secret fetish.
Charlie is dating a woman whose personality and life are like his mother’s.
Alan is overjoyed by the prospect of Judith remarrying, as he would no longer have to pay alimony. Alan gets Charlie to help him when it looks like the marriage maybe derailed due to Jake’s dislike of his mother’s fiancé.
Alan tries to hire his ex-wife's lawyer to help him win custody over the dog he and Kandi shared.
Charlie tries to surf to impress Dottie, a beautiful woman he just met, but after he nearly drowns he is convinced that he saw his late father.
Charlie finally tells Alan the truth about why he did not marry Mia. Charlie and Alan deal with a noisy neighbor.
Charlie returns to his bachelor lifestyle after Alan moves out of the house. Alan suffers a breakdown after his divorce from Kandi.
