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Alan and Judith meet with Jake's teacher to discuss his lack of interest in school. Alan ends up falling for Francine as a friend since he's so desperate for intelligent conversation with Kandi.
Alan tries to win back Kandi; Charlie ends up dating her mother Mandi; and Judith ends up with her father, Andy.
Charlie is surprised to find out that Kandi has been living with Alan in his house for the past three weeks. Alan is having trouble getting Kandi a job and Charlie is going through a dry spell.
Alan is having financial troubles trying to pay Judith's alimony and his girlfriend Kandi's bills. Charlie tries to convince him to dump Kandi.
When Charlie is nominated for a jingle award, he refuses to go since his rival always wins. His family manages to convince him to go. Meanwhile, Rose comes to Charlie with her boyfriend problems.
Alan tries to decide whether he should bring his younger girlfriend, Kandi, to Jake's birthday party where she'd meet Judith. Meanwhile, Rose tries to get her boyfriend to dress and act more like Charlie.
When Mia tries to make Charlie healthier, he continues to sneak drinks, cigars and hamburgers behind her back. He needs to decide if he's in love or just whipped.
Charlie continues to attempt to sleep with his girlfriend, Mia, when a sex-craved ex-girlfriend of his, Kandi shows up and complicates things. Alan ends up dating her.
Charlie and Mia attempt to start a relationship that's not based on sex by not having any. Charlie makes an inappropriate suggestion involving other women.
When Alan becomes insecure over the fact Jake doesn't want to spend time with him, Charlie begins seeing a therapist.