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- Season 5 overviewSep 24, 2007-May 19, 200819 episodesSeason 5 episodes1. Large Birds, Spiders and Mom Sep 24, 2007
- Charlie and Alan try to prepare Jake for his first day of junior high.
- 2. Media Room Slash Dungeon Oct 1, 2007
- Charlie reacts oddly after an evening with his mother.
- 3. Dum Diddy Dum Diddy Doo Oct 8, 2007
- Charlie lets Alan set him up with a woman his own age.
- 4. City of Great Racks Oct 15, 2007
- Although Charlie is getting closer to Linda, he begins to see Rose's face wherever he looks.
- 5. Putting Swim Fins on a Cat Oct 22, 2007
- Charlie has to entertain his girlfriend's 4-year-old son; Alan becomes a human guinea pig.
- 6. Help Daddy Find His Toenail Oct 29, 2007
- Charlie's girlfriend is embarrassed to be seen with him; Jake sneaks out to go to a concert.
- 7. Our Leather Gear Is in the Guest Room Nov 5, 2007
- Charlie and Alan butt heads over Alan's place in the house.
- 8. Is There a Mrs. Waffles? Nov 12, 2007
- Charlie finds success as a children's singing star, which makes Alan miserable.
- 9. Tight's Good Nov 19, 2007
- Charlie tries to resist an attraction to his soon-to-be stepsister (Jenny McCarthy).
- 10. Kinda Like Necrophilia Nov 26, 2007
- Alan seeks revenge when he discovers that Charlie stole his high-school girlfriend.
- 11. Meander to Your Dander Mar 17, 2008
- Charlie offers Alan pointers on how to break up with a woman.
- 12. A Little Clammy and None Too Fresh Mar 24, 2008
- Rose comes back from England and takes care of sick Charlie in a very strange way.
- 13. The Soil Is Moist Mar 31, 2008
- Alan's date, who happens to be a friend of his ex, reveals a secret about Judith's sex life.
- 14. Winky-Dink Time Apr 14, 2008
- Charlie goes with Jake on a double date and sets up Alan with a prostitute.
- 15. Rough Night in Hump Junction Apr 21, 2008
- Alan fears that Charlie's womanizing is getting out of control.
- 16. Look at Me, Mommy, I'm Pretty Apr 28, 2008
- Alan plans Evelyn's wedding; Charlie pursues his future stepsister.
- 17. Fish in a Drawer May 5, 2008
- A CSI team investigates a mysterious death at Charlie's house.
- 18. If My Hole Could Talk May 12, 2008
- Charlie discovers he is attracted to an older woman who writes self-help books; Jake and Alan fight.
- 19. Waiting for the Right Snapper May 19, 2008
- Charlie meets the daughter of the woman he's dating.