When Judith announces she is going to remarry, Charlie and Alan must convince her fiancé to proceed with the nuptials after he displays signs of cold feet, so that Alan can discontinue alimony payments to Judith.
After a bout with insomnia, Alan is escorted home from a midnight run on the beach by the local sheriff's department. Jake fights back when Charlie goes back on his word about not dating his friend's mother.
Charlie tries to set up Alan with the sexy and rich new next-door neighbor who is looking to settle down. But when Charlie discovers her secret history as a drunken slut, he decides to go after her himself.