Alan has a difficult time coping when Lyndsey breaks up with him.

Alan and Walden end up partying too hard as they try to cheer up Herb.

After a fight with Walden, Alan decides to move in with Herb.

Alan is faced with relationship trouble when he does not give Lyndsey a key to the beach house; Walden, Alan, Herb and Billy commiserate about relationships.

Jake is pressured to make a decision about his future.

Upon his release from the hospital, Alan is met with a slew of challenges that test his ability to cope.

Alan prepares Walden for a date with Bridget, while Jake decides to emulate Walden and drop out of school.

Judith is pregnant with a baby girl and Alan is convinced he is the father.

Charlie borrowed money from Alan and on the day he is supposed to pay him back, Alan goes to ask Charlie for the money. He again finds Charlie in bed…

Alan finds out some surprising information about Judith’s sex life when he decides to go on a date with one of her friends.

Alan looks forward to Judith’s wedding, while Charlie and Myra continue their romance.

Charlie takes a liking to Myra, the witty sister of Judith’s fiancé, Herb.

Jake shares that he has heard his mother having sex with her fiancée, Herb; this revelation brings up a repressed memory for Charlie. This leads Charlie to seek help from…

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…

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…

Judith is dating Jake’s pediatrician, and Alan is upset until Charlie points out that if she remarries, his alimony payments will end.