Charlie takes a liking to Myra, the witty sister of Judith's fiancé, Herb.
Charlie's friends and family put a crimp in his plan for a romantic Christmas Eve date. When Evelyn sees who the date is, she goes to great lengths to force a wedge between them.
Alan suffers from insomnia. He visits his psychiatrist (Jane Lynch), 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 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 returns to his bachelor lifestyle after Alan moves out of the house. Alan suffers a breakdown after his divorce from Kandi.