Season 5

2007 · 19 episodes

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

1Large Birds, Spiders and MomJake 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.
2Media Room Slash DungeonCharlie acts strange after spending an evening with his mother, and a woman Alan slept with behaves oddly the next morning.
3Dum Diddy Dum Diddy DooAlan 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.
4City of Great RacksCharlie and Linda get closer to consummating their relationship, but Charlie has trouble focusing when he begins to see Rose's face everywhere he turns.
5Putting Swim Fins on a CatCharlie has to come up with ways to keep his girlfriend's 4-year-old amused; Alan becomes a test subject.
6Help Daddy Find His ToenailCharlie's girlfriend is embrassed to go out in public with him. Meanwhile, Jake sneaks out to attend a concert.
7The Leather Gear Is in the Guest RoomAfter Alan and Charlie have a fight about Alan's role in the house. Alan packs Jake up and moves in with his mother.
8Is There a Mrs. Waffles?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.
9Shoes, Hats, Pickle Jar LidsCharlie fights his attraction for Teddy's daughter.
10Kinda Like NecrophiliaAlan 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.
11Meander to Your DanderWhen Alan finds himself wanting to break up with a woman, Charlie offers his expertise.
12A Little Clammy and None Too FreshRose returns from England, and plays nurse rather oddly for an ill Charlie.
13The Soil Is MoistAlan finds out some surprising information about Judith's sex life when he decides to go on a date with one of her friends.
14Winky-Dink TimeCharlie double-dates with Jake and fixes Alan up with a hooker.
15Rough Night in Hump JunctionAlan feels Charlie is unable to control his womanizing ways.
16Look at Me Mommy, I'm PrettyAlan makes wedding plans for Evelyn and Teddy, while Charlie figures out how to get more acquainted with his future step-sister.
17Fish in a DrawerCSIs investigate a death at Charlie's house.
18If My Hole Could TalkCharlie's attracted to an older self-help author. Alan and Jake clash over a project for school.
19Waiting for the Right SnapperWhen Charlie meets Angie's soon to be daughter-in-law, he realizes it's not for the first time.

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