Jake wants to go home to his mom after he gets sick, prompting Alan to think he's a failure as a husband and now as a father.

Alan and Charlie have encounters with some highly libidinous soccer moms, but with two very different outcomes.

The guys go to Evelyn's house to meet the new man she's dating, and Charlie realizes the man's daughter is a woman he's trying to avoid.

Judith is upset with Alan and Charlie when she learns that a surfer who uses Charlie's shower walks around half naked in front of Jake . Then Alan's worried when Judith and the surfer become friends.

Alan tricks Charlie into joining him and Judith in leading Jake and his classmates in the school's annual music show.

When Alan is surprised to see that Judith has had a makeover and is dating a man, he decides to have Charlie help him transform his image.

Berta's granddaughter spends the day at Charlie's, which isn't a problem until he learns she's a beautiful, rebellious 16-year-old.

Charlie nurses an ailing Alan back to health so they can go on a double date with two sisters, one of whom Charlie's been wanting to date for a long time.

Charlie's financial manager informs the carefree jingle writer that he spends money faster than his royalty checks come in, and now he must go on a budget.

Charlie is stunned to learn his ex-girlfriend is now a man.

Judith's devious siren sister stirs things up at Jake's 11th birthday party when she hits on Alan. Meanwhile, Evelyn brings alcohol and has a party of her own.

Jake's sullen mood baffles and bothers the family and prompts Alan and Judith to take him to a child psychologist.

When Jake repeats one of Charlie's sexist remarks in front of Judith's support group, the women convince Judith to stop Jake's visits with his dad and Charlie.

Charlie has a pregnancy scare involving one of his one-night stands and decides to go for the big "V," and we're not talking Vegas.

Alan learns that Charlie belongs to an exclusive men's group, and he begs his brother to let him join.

Judith is dating Jake's pediatrician, and Alan is upset until Charlie points out that if she remarries, his alimony payments will end.

Charlie tries to save Jake from school suspension for giving his teacher (Missi Pyle) the finger by romancing her, but his several attempts fail every time.

Charlie meets his match when he falls for a woman who's better at playing hard to get than he is.

When Charlie leaves the house to avoid a date that he can't stand, he ends up at a coffee shop, where he meets his old girlfriend Lisa. He finds out that she broke up with her husband, and now has a child. Now he must try to convince Lisa that he's okay with her having a child. While Jake tries to justify to his father why he isn't doing so well in school.

Alan is jealous of Charlie when an old classmate, who's now a beautiful woman, seems to be more interested in Charlie.

The brothers throw out their mother, after she insults the way Alan is raising Jake. When Alan and Charlie ignore her phone calls, to get their attention she ends up in the hospital. When Alan and Charlie show up at the hospital they aren't sure if she's faking, and try to call her bluff.

Alan starts to worry about a medical procedure that he is facing, and to get his mind off it, Charlie suggests they go to Las Vegas.

Charlie is invited to a party hosted by a gay ad-executive named Eric, so Charlie asks Alan to pretend that he's his life partner. While at the party, Charlie meets Eric's ex-wife Pamela, and tries to sleep with her without Eric finding out.

Charlie finds himself re-examining his wild ways when an old friend dies and begins to feel that his time on Earth may be drawing to a close.