Evelyn gets a new boyfriend, Teddy, who bonds with Alan and Charlie by taking them to Las Vegas. The boys confront their feelings about their mother dating and men coming in and out of their lives.

Charlie is shocked when the handyman working on his house beats him out for Chloe's affections. Alan has no sympathy for Charlie’s distress.

Alan asks Charlie to help Jake with his book report so he can take the time to go to the DMV. Charlie agrees and then decides he wants to go to the race track and takes Jake with him. Alan is conned at the DMV.

Alan and Charlie re-examine their sexual identities after Alan befriends Greg, a gay man. Meanwhile, Jake has a crush on Greg's daughter.

Alan looks forward to Judith's wedding, while Charlie and Myra continue their romance.

Alan is overjoyed at the prospect of giving Judith her last alimony check. Charlie decides to go along for the ride and meets Herb's sister Myra. Charlie and Myra bond over a common problem, their dislike for Judith.

Alan tries to bond with Jake when he realizes that his childhood is almost over. Kandi pursues a career in acting.

After Evelyn tells Alan and Charlie how she feels about there being no mourners at her friend's funeral, the boys share their feelings that this could also be the case at hers. Evelyn tries to prove them wrong by introducing them to a couple she helped adopt a boy from China.

Charlie's young, hot girlfriend takes him to a new club. She invites Alan to meet one of her friends but the men are shocked to learn that they are considered as being "old".

Rose is moving to London, and Charlie is surprised by his reaction to the news. Alan lies to a woman he met online.

Charlie sets Alan up with their new neighbor, but he gets jealous when the two form a bond.

Jake shares that he has heard his mother having sex with her fiancé, Herb; this revelation brings up a repressed memory for Charlie. This leads Charlie to seek help from Rose.

Berta discovers that Alan has been dating her daughter Naomi.

Charlie's friends and family put a crimp in his plan for a romantic Christmas Eve date. When Evelyn sees who the date is, she goes to great lengths to force a wedge between them.

Worrying Charlie may get rid of one of them, Berta and Lydia fight over him. Meanwhile, Kandi does everything she can to stop Alan from selling their condo.

Charlie gets tired of Alans mooching and reaches the breaking point during the brothers double date. Jake is left home alone for the first time.

Alan suffers from insomnia. He visits his psychiatrist, who reveals that the cause of Alan's sleepless nights is his jealousy towards Charlie, and his inability to glide through life.

Berta's daughter, Naomi is pregnant and Berta drags Charlie with her when she confronts the baby’s father. Alan reveals a secret fetish.

Charlie is dating a woman whose personality and life are like his mother’s.

Alan is overjoyed by the prospect of Judith remarrying, as he would no longer have to pay alimony. Alan gets Charlie to help him when it looks like the marriage maybe derailed due to Jake’s dislike of his mother’s fiancé.

Alan tries to hire his ex-wife's lawyer to help him win custody over the dog he and Kandi shared.

Charlie tries to surf to impress Dottie, a beautiful woman he just met, but after he nearly drowns he is convinced that he saw his late father.

Charlie finally tells Alan the truth about why he did not marry Mia. Charlie and Alan deal with a noisy neighbor.

Charlie returns to his bachelor lifestyle after Alan moves out of the house. Alan suffers a breakdown after his divorce from Kandi.