Charlie's life gets a little more complicated when his brother, Alan, and son, Jake, move in with him after his wife confesses her lesbian lifestyle and throws him out of the house. Alan later leaves after finding his son playing poker and moves in with his mother, Evelyn. Charlie realizes how lonely it is without them and invites them back.

Charlie finds it hard to enforce the rules Alan has set out for his son. After Jake lures a flock of sea gulls into his room, Charlie gets very upset. Jake tries to get Charlie to forgive him. Alan starts doing chores and errands for Judith, trying to get them back together. After one of his tasks, she kisses him, leading him to believe that things will be back to normal.

After a trip to Disneyland, Jake gets sick and wants to go to Judith's house so she can take care of him. Alan gets saddened over this because he is losing his wife and son. Charlie takes him to a bar, and after drinking, they end up at their mother's house trying to tell her what they think of her, but not successful in the process.

Berta, the housekeeper, quits after experiencing Alan's demanding ways. Alan decides he could be the housekeeper, but does not work. Alan decides to hunt her down and bring her back, leaving Charlie to get ready for dinner with his mother and grandparents. Charlie also tries to get Rose to date other guys, both tasks become harder than expected.

After a trip to Las Vegas Charlie decides to go to Jake's soccer game like he promised. There, he meets a soccer mom and they hit it off. Alan goes to a meeting with some soccer moms about creating a newsletter, but does not realize they have other plans for the night.

Charlie gets in over his head after he tells Jake to avoid certain calls he doesn't want which creates a dinner plan for Charlie and his mother. When Charlie meets her new boyfriend's daughter, he realizes it is one of the people he is trying to avoid.

For a class assignment, Jake draws the tattooed buttocks of one of Charlie's surfer friends, which in turn, worries his mother. Alan then starts to get worried about Judith when she becomes friends with the surfer girl.

Alan tricks Charlie in leading Jake and his classmates in the music show along with Alan and Judith.

Jake befriends one of Charlie's one-night stands, which Charlie does not like as it furthers the relationship that Charlie does not want to continue.

To try and prove to his girlfriend that he is a family man, Charlie invites Lisa over for Thanksgiving dinner at his house.

After bumping into Judith and her new boyfriend at the movies, Alan decides to change his look to try and get back into the dating scene, and to impress his son.

Berta becomes forced to bring her granddaughter Prudence to work for a day. The boys like this because they get very preoccupied with her.

Charlie gets a double date with a hot neighbor and her sister and needs to take Alan along. The trouble is, Alan got sick from Jake so Charlie takes him to a steam room to heal him. It works for Alan, but Charlie becomes ill, but won't cancel the date at any cost.

Charlie's accountant Stan tries to explain Charlie's financial problems to him.

Charlie falls for a seemingly crazy woman named Franky against Alan's constant arguments about the woman.

Frankie tells Charlie and Alan why both her and her daughter are on the run, and Frankie's daughter gets a crush on Jake.

Charlie gets offended after Alan chooses harebrained cousins as Jake's legal guardians in the event of his death.

Charlie is stunned to find out that one of his ex-girlfriends had a sex change operation.

At Jake's birthday party Judith's sister Liz hits on Alan while Evelyn prefers to drink alcohol than eat cake.

When Jake starts playing guitar non-stop, Judith thinks it is because he is having a hard time dealing with the divorce. She suggests that he sees a therapist, which Alan does not agree with at the beginning, but agrees later on.

Charlie puts Alan's divorce settlement into jeopardy when he sleeps with his attorney, Laura.

Charlie tries to cure Alan of his recent sleepwalking adventures; Jake goes and sees a therapist.

Charlie tries to sweet talk Judith's support-group with other divorcees into letting Jake still spend weekends at his place.

Charlie heads to the doctor for a vasectomy after a recent pregnancy scare.