Kelley West

Alan's expectations for a first date with Nancy (Kelley West), a woman he met while shopping for groceries, are far exceeded when she introduces him to a world of sex he never knew existed. Charlie is happy that his brother is getting to experience the kind of sex life he's always enjoyed, but he's not thrilled to take responsibility for Jake while Alan has his every fantasy fulfilled. When Alan starts thinking he loves this woman, Charlie realizes he must take action.

Charlie and Alan take Jake to a friend's house and go out for some sibling bonding at the movies, but their night is ruined when Alan freaks out after convincing himself that Jake was too eager to spend the weekend away from him. Recognizing that desperate times call for desperate measures, Charlie begins seeing a psychiatrist, Dr. Linda Freeman (Jane Lynch -- "The 40-Year-Old Virgin"), ostensibly to learn how to cope with his brother's ever-increasing emotional instability.