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.
Episode 2 - Media Room Slash Dungeon
Charlie acts strange after spending an evening with his mother, and a woman Alan slept with behaves oddly the next morning.
Episode 3 - Dum Diddy Dum Diddy Doo
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 Alans ex girlfriends. Charlies date backfires the following morning, when he ends up in court in front of the judge.
Episode 4 - City of Great Racks
Charlie and Linda get closer to consummating their relationship, but Charlie has trouble focusing when he begins to see Roses face everywhere he turns.
Episode 5 - Putting Swim Fins on a Cat
Charlie has to come up with ways to keep his girlfriends 4 year old amused Alan becomes a test subject.
Episode 6 - Help Daddy Find His Toenail
Charlies girlfriend is embrassed to go out in public with him. Meanwhile, Jake sneaks out to attend a concert.
Episode 7 - The Leather Gear Is in the Guest Room
After Alan and Charlie have a fight about Alans role in the house. Alan packs Jake up and moves in with his mother.
Episode 8 - Is There a Mrs. Waffles
Charlie writes a childrens song and finds success as Charlie Waffles. The children love him and the mothers seem to as well. Charlies new found fame irritates Alan.
Episode 9 - Tights Good
Charlie fights his attraction for Teddys daughter.
Episode 10 - Kinda Like Necrophilia
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.
Episode 11 - Meander to Your Dander
When Alan finds himself wanting to break up with a woman, Charlie offers his expertise.
Episode 12 - A Little Clammy and None Too Fresh
Rose returns from England, and plays nurse rather oddly for an ill Charlie.
Episode 13 - The Soil is Moist
Alan finds out some surprising information about Judiths sex life when he decides to go on a date with one of her friends.
Episode 14 - Winky Dink Time
Charlie double dates with Jake and fixes Alan up with a hooker.
Episode 15 - Rough Night in Hump Junction
Alan feels Charlie is unable to control his womanizing ways.
Episode 16 - Look at Me, Mommy, Im Pretty
Alan makes wedding plans for Evelyn and Teddy, while Charlie figures out how to get more acquainted with his future step sister.
Episode 17 - Fish in a Drawer
CSIs investigate a death at Charlies house.
Episode 18 - If My Hole Could Talk
Charlies attracted to an older self help author. Alan and Jake clash over a project for school.
Episode 19 - Waiting for the Right Snapper
When Charlie meets Angies soon to be daughter in law, he realizes its not for the first time.