Season 5

2007 · 19 episodes · 6h 43m in all · 7.4/10

Charlie finds himself in unfamiliar territory with real feelings, Alan keeps stumbling through relationships, and Jake edges from boyhood into teenage antics.

1. Large Birds, Spiders and Mom
24 Sept 2007 · 20 min · 7.6/10
Jake is getting ready to start a new school as he graduates to Junior High. Alan and Charlie take him school shopping and find themselves in trouble.
2. Media Room Slash Dungeon
1 Oct 2007 · 22 min · 6.3/10
Charlie acts strange after spending an evening with his mother, and a woman Alan slept with behaves oddly the next morning.
3. Dum Diddy Dum Diddy Doo
8 Oct 2007 · 21 min · 7.2/10
Alan convinces Charlie that he needs to date more respectable women and sets him up with a judge. The two double date and their waitress happens to be one of Charlie's ex-girlfriends. Charlie's date backfires the following morning, when he ends up in court in front of the judge.
4. City of Great Racks
15 Oct 2007 · 22 min · 7.2/10
Charlie and Linda get closer to consummating their relationship, but Charlie has trouble focusing when he begins to see Rose's face everywhere he turns.
5. Putting Swim Fins on a Cat
22 Oct 2007 · 22 min · 7.5/10
Charlie has to come up with ways to keep his girlfriend's 4-year-old amused; Alan becomes a test subject.
6. Help Daddy Find His Toenail
29 Oct 2007 · 21 min · 7.3/10
Charlie's girlfriend is embrassed to go out in public with him. Meanwhile, Jake sneaks out to attend a concert.
7. The Leather Gear Is in the Guest Room
5 Nov 2007 · 20 min · 7.3/10
After Alan and Charlie have a fight about Alan's role in the house. Alan packs Jake up and moves in with his mother.
8. Is There a Mrs. Waffles?
12 Nov 2007 · 20 min · 7.9/10
Charlie writes a children's song and finds success as Charlie Waffles. The children love him and the mothers seem to as well. Charlie's new found fame irritates Alan.
9. Shoes, Hats, Pickle Jar Lids
19 Nov 2007 · 20 min · 7.7/10
Charlie fights his attraction for Teddy's daughter.
10. Kinda Like Necrophilia
26 Nov 2007 · 22 min · 7.6/10
Alan finds out that Charlie stole his girlfriend and works on a plan to get back at Charlie, even though this happened when they were in high school.
11. Meander to Your Dander
17 Mar 2008 · 22 min · 7.8/10
When Alan finds himself wanting to break up with a woman, Charlie offers his expertise.
12. A Little Clammy and None Too Fresh
24 Mar 2008 · 22 min · 7.5/10
Rose returns from England, and plays nurse rather oddly for an ill Charlie.
13. The Soil Is Moist
31 Mar 2008 · 20 min · 7.4/10
Alan finds out some surprising information about Judith's sex life when he decides to go on a date with one of her friends.
14. Winky-Dink Time
14 Apr 2008 · 22 min · 7.4/10
Charlie double-dates with Jake and fixes Alan up with a hooker.
15. Rough Night in Hump Junction
21 Apr 2008 · 21 min · 7.8/10
Alan feels Charlie is unable to control his womanizing ways.
16. Look at Me Mommy, I'm Pretty
28 Apr 2008 · 22 min · 7.6/10
Alan makes wedding plans for Evelyn and Teddy, while Charlie figures out how to get more acquainted with his future step-sister.
17. Fish in a Drawer
5 May 2008 · 21 min · 7.1/10
CSIs investigate a death at Charlie's house.
18. If My Hole Could Talk
12 May 2008 · 21 min · 7.1/10
Charlie's attracted to an older self-help author. Alan and Jake clash over a project for school.
19. Waiting for the Right Snapper
19 May 2008 · 22 min · 7.4/10
When Charlie meets Angie's soon to be daughter-in-law, he realizes it's not for the first time.