Evelyn's boyfriend, Teddy, invites Alan and Charlie to go with him to Las Vegas on his private jet. The boys confront their individual 'daddy issues'

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.

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. Charlie's date backfires the following morning, when he ends up in court in front of the judge.

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 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.

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.