When Alan injures himself after falling off the roof, Charlie agrees to take care of Jake for the weekend.
Alan enlists Charlies's aid in answering phones at his chiropractic office, a move that turns out to be a bad idea when Charlie turns the office into a brothel.
Charlie stages an elaborate intervention to keep Alan and Judith from reuniting when he finds out they've been dating.
Alan allows Berta to stay at Charlie's house on a temporary basis, a move which puts the brothers at odds.
A woman declares her love for Charlie only to have him respond inappropriately and Jake seeks Charlie's advice about a girl at school that likes him.
Charlie is ecstatic about his new wild, sexually uninhibited Goth girlfriend, but Alan is convinced that she's put an evil curse on him.When Charlie is invited to a coven party and sees the effect she is having on him the next morning, he decides to break it off but she proves to be difficult to get rid of without the malevolent intervention of his mother.
Charlie is confronted by the father of his stalker, Rose, who demands to know Charlie's intentions towards his daughter.
After Charlie is rejected by an attractive ballet teacher, he cons Jake into taking dance lessons to advance his cause.
A wealthy, elderly woman vies for Alan's affections.
Alan organizes a dinner to celebrate a positive newspaper article about him.
Alan's new girlfriend turns out to be a Martha Stewart-like control freak bent on taking over the house during Christmas.
Charlie starts seeing a therapist in order to deal with Alan's emotional insecurities.
No one believes that Charlie has been in a serious relationship for a month without having sex.
Charlie plans a romantic evening with Mia in the hopes of consummating their relationship and Alan starts dating a woman half his age.
Charlie sneaks beer, cigars and hamburgers when he finds that he can't hack the healthy lifestyle that Mia has imposed on him.
Alan tries to avoid bringing his 22 year-old girlfriend to Jake's birthday party.
Charlie boycotts an advertising banquet where he is up for an award due to the fact that he keeps losing to his nemesis, Archie.
Alan is in financial dispair because of taking on his girlfriend's bills and Charlie makes up a lie to Judith for him when he can't make his alimony payment on time.
Charlie discovers he has a new roommate, that Kandi has been living with Alan which creates lots of tension in the house. To make matters worst Charlie has been having a dry spell with women.
Kandi, Alan's hot young girlfriend leaves him and goes to stay with his ex-wife Judith, Alan tries to win her back but Judith has turned her against him.
Lacking the stimulation of an intelligent conversation, Alan finds more in common with Jake's teacher than Kandi. His efforts to not lead her on prove complicated though as Charlie entertains himself by compounding the situation for Alan.
Jake gets invited to his first boy-girl party and needs Charlie's wisdom on hooking up with the chicks. Allen feels shorted, not just that this should be a father-son bonding moment but also that Charlie never gave him the same advice. He is glad that Jake got such expert advice though, especially when it pays off for Jake.
When Charlie finds out that Mia is in town with her dance troupe and has invited him to her performance, he opts not to go and tries to convince Alan (and himself) that he's over her.
Happily ever after, or not. Charlie and Mia's big day is finally here but when the families meet things immediately start to go down-hill.Rose takes the news of the engagement hard, and makes some interesting plans of her own.