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

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.

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 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 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.

Charlie finally tells Alan that he didn't marry Mia because she wanted Alan and Jake to move out of the house, but Alan finds a hole in his logic. Charlie and Alan deal with a noisy neighbor who constantly sings all the time, who happens to be Steven Tyler.

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 takes a liking to Myra, the witty sister of Judith's fiancé, Herb.

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

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

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.

Jake gets lucky after Charlie takes him to the racetrack. Meanwhile, Alan has a difficult time at the DMV.

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

Charlie sets Alan up with their new neighbour. But he gets jealous when the two form a bond.

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".

Evelyn's boyfriend, Teddy, invites Alan and Charlie to go with him to Las Vegas on his private jet. The boys confront their individual 'daddy issues'

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

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

Berta discovers that Alan has been dating her daughter Naomi.

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

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

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

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 her funeral. Evelyn tries to prove them wrong by introducing them to a couple she help adopt a boy from China. The boys return fire by inviting the young man to a play date with Jake.