Jake is getting ready to start a new school as he advances to junior high. Alan and Charlie take him school shopping and find themselves in trouble.
Charlie acts strange after spending an evening with his mother, and a woman Alan slept with behaves oddly the next morning.
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. Desperate for a second chance, Charlie goes to great lengths to speak to her again.
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.
Charlie has to come up with ways to keep his girlfriend's 4-year-old son amused. Meanwhile, Alan becomes a test subject.
Charlie's girlfriend is embarrassed to go out in public with him. Meanwhile, Jake sneaks out to attend a concert.
After Alan and Charlie have a fight about Alan's role in the house, Alan packs Jake up and moves in with his mother.
Charlie writes a childrens song and finds success as Charlie Waffles. The kids and their parents love him. However, Charlie's new found fame irritates Alan.
Charlie fights his attraction for Teddy's daughter.
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.
When Alan finds himself wanting to break up with a woman, Charlie offers his expertise.
Rose returns from England, and plays nurse for an ill Charlie. Alan feels Jake pulling away from him.
Alan finds out some surprising information about Judith's sex life when he decides to go on a date with one of her friends.
Charlie double-dates with Jake and fixes Alan up with a hooker.
Alan feels Charlie is unable to control his womanizing ways.
Alan makes wedding plans for Evelyn and Teddy, while Charlie figures out how to get more acquainted with his future step-sister, Courtney.
CSIs investigate a death at Charlie's house.
Charlie's attracted to an older self-help author. Alan's insistance that Jake complete his Taming of the Shrew book report is hampered by Jake's continually losing the book.
When Charlie meets the fiancée of Angie's grown-up son, he realizes it's not for the first time. Alan tries to get Jake to study for his algebra final.