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- Season 4 overviewSep 18, 2006-May 14, 200724 episodesSeason 4 episodes1. Working for Caligula Sep 18, 2006
- Charlie returns to his bachelor lifestyle; Alan breaks down following his second divorce.
- 2. Who's Vod Kanockers? Sep 25, 2006
- Charlie tells Alan the truth about his breakup with Mia; a famous neighbor causes trouble.
- 3. The Sea Is a Harsh Mistress Oct 2, 2006
- Charlie is convinced he saw his late father while having a near-death experience.
- 4. A Pot-Smoking Monkey Oct 9, 2006
- After their split, Alan wants to gain custody of his and Kandi's dog.
- 5. A Live Woman of Proven Fertility Oct 16, 2006
- Alan and Charlie try to help Herb and Jake bond.
- 6. Apologies for the Frivolity Oct 23, 2006
- Charlie does not realize that his latest girlfriend is a younger version of his mother.
- 7. Repeated Blows to His Unformed Head Nov 6, 2006
- Charlie helps Berta confront the man who impregnated her daughter.
- 8. Release the Dogs Nov 13, 2006
- Jake pleads with Charlie not to date the mother of a girl he likes..
- 9. Corey's Been Dead for an Hour Nov 20, 2006
- Charlie and Alan go on a double date, leaving Jake home alone for the first time.
- 10. Kissing Abraham Lincoln Nov 27, 2006
- Charlie must choose between his girlfriend and his housekeeper.
- 11. Walnuts and Demerol Dec 11, 2006
- Charlie finds himself throwing an unwanted, unplanned holiday party.
- 12. Castrating Sheep in Montana Jan 8, 2007
- Berta learns that Alan has been dating her daughter (Sara Rue).
- 13. Don't Worry, Speed Racer Jan 22, 2007
- Jake tells Charlie and Alan that he often overhears Judith and Herb making out.
- 14. That's Summer Sausage, Not Salami Feb 5, 2007
- Charlie has second thoughts after setting Alan up with their new neighbor (Brooke Shields).
- 15. My Damn Stalker Feb 12, 2007
- Charlie must face his feelings when Rose announces she is moving to London.
- 16. Young People Have Phlegm Too Feb 19, 2007
- A more mature woman helps rebuild Charlie's ego when he becomes insecure.
- 17. I Merely Slept With a Commie Feb 26, 2007
- Evelyn makes Charlie and Alan regret saying that she will not have any mourners at her funeral.
- 18. It Never Rains in Hooterville Mar 19, 2007
- Alan tries to bond with Jake; Kandi's new career.
- 19. Smooth as a Ken Doll Apr 9, 2007
- Charlie gets close to Herb's witty sister, as Judith and Herb's wedding nears.
- 20. Aunt Myra Doesn't Pee a Lot Apr 16, 2007
- Alan prepares Jake for Judith's wedding; Charlie continues his fling with Herb's sister.
- 21. Tucked, Taped and Gorgeous Apr 23, 2007
- Alan's friendship with a gay single dad prompts him to re-examine his sexual identity.
- 22. Mr. McGlue's Feedbag Apr 30, 2007
- Jake has a windfall at the track with Charlie; Alan visits the Department of Motor Vehicles.
- 23. Anteaters. They're Just Crazy-Lookin' May 7, 2007
- Charlie loses a woman to the young, handsome handyman (Enrique Iglesias) working at his house.
- 24. Prostitutes and Gelato May 14, 2007
- Evelyn's new boyfriend invites Charlie and Alan to Las Vegas.