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When Jake gets in trouble for giving his teacher the middle finger, Charlie tries to help by romancing his teacher.
Judith is dating Jake's pediatrician, Dr. Melnick (Ryan Stiles), which initially upsets Alan until Charlie points out if they get married his alimony payments end.
When Alan learns that Charlie belongs to an exclusive men's club that includes celebrities such as Henry Dean Stanton, Sean Penn and Elvis Costello, Alan wants in.
A woman that Charlie had sex with thinks she's pregnant. After this close call, Charlie goes in to get a vasectomy.
Charlie sweet talks Judith's divorcee support-group to continue to let Alan have weekend custody of Jake and let him stay at Charlie's.
Charlie attempts to cure Alan of his recent problem of sleep walking. Meanwhile, Jake goes to see his new therapist.
Charlie jeopardizes Alan's divorce settlement when he sleeps with his beautiful attorney, Laura (guest star Heather Locklear).
When Jake won't stop playing the guitar, Judith believes he's having a tough time adjusting to her and Alan's divorce. Judith wants to send Jake to a therapist to help him.
Judith's sister, Liz (Teri Hatcher) is in town and hits on Alan at Jake's birthday party. Evelyn chooses alcohol over birthday cake.
Charlie is stunned to learn that his ex-girlfriend, Jill, is now a man, Bill (Chris O'Donnell) and dating his mother.
