Charlie returns to his bachelor lifestyle after Alan moves out of the house. Alan suffers a breakdown after his divorce from Kandi.
Episode 2 - Whos Vod Kanockers
Charlie finally tells Alan the truth about why he did not marry Mia. Charlie and Alan deal with a noisy neighbour.
Episode 3 - The Sea is a Harsh Mistress
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.
Episode 4 - A Pot Smoking Monkey
Alan tries to hire his ex wifes lawyer to help him win custody over the dog he and Kandi shared.
Episode 5 - A Live Woman of Proven Fertility
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 may be derailed due to Jakes dislike of his mothers fianc.
Episode 6 - Apologies for the Frivolity
Charlie is dating a woman whose personality and life are like his mothers.
Episode 7 - Repeated Blows to His Unformed Head
Bertas daughter, Naomi, is pregnant and Berta drags Charlie with her when she confronts the babys father. Alan reveals a secret fetish.
Episode 8 - Release the Dogs
Alan suffers from insomnia. He visits his psychiatrist (Jane Lynch), who reveals that the cause of Alans sleepless nights is his jealousy towards Charlie, and his inability to glide through life.
Episode 9 - Coreys Been Dead for an Hour
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.
Episode 10 - Kissing Abe Lincoln
Charlie must choose between his girlfriend and his housekeeper Alan looks to sell Kandis condo, but sex keeps getting in the way.
Episode 11 - Walnuts and Demerol
Charlies 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.
Episode 12 - Castrating Sheep in Montana
Berta discovers that Alan has been dating her daughter (Sara Rue).
Episode 13 - Dont Worry, Speed Racer
When Jake tells Charlie and Alan that he often overhears Judith and Herb (Ryan Stiles) making out, it triggers a repressed memory for Charlie.
Episode 14 - Thats Summer Sausage, Not Salami
Charlie has second thoughts after setting Alan up with their new neighbor (Brooke Shields)..
Episode 15 - My Damn Stalker
Rose is moving to London, and Charlie is surprised by his reaction to the news. Alan lies to a woman he met online.
Episode 16 - Young People Have Phlegm Too
Charlies 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.
Episode 17 - I Merely Slept with a Commie
After Evelyn tells Alan and Charlie how she feels about there being no mourners at her friends 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.
Episode 18 - It Never Rains in Hooterville
Alan tries to bond with Jake when he realizes that his childhood is almost over. Kandi pursues a career in acting.
Episode 19 - Smooth as a Ken Doll
Charlie takes a liking to Myra, the witty sister of Judiths fianc, Herb.
Episode 20 - Aunt Myra Doesnt Pee a Lot
Alan looks forward to Judiths wedding, while Charlie and Myra continue their romance.
Episode 21 - Tucked, Taped and Gorgeous
Alan and Charlie re examine their sexual identities after Alan befriends Greg, a gay man. Meanwhile, Jake has a crush on Gregs daughter.
Episode 22 - Mr. McGlues Feedbag
Jake gets lucky after Charlie takes him to the racetrack. Meanwhile, Alan has a difficult time at the DMV.
Episode 23 - Anteaters. Theyre Just Crazy Lookin
Charlie is shocked when the handyman working on his house beats him out for Chloes affections. Alan has no sympathy for Charlies distress.
Episode 24 - Prostitutes and Gelato
Evelyns boyfriend, Teddy, invites Alan and Charlie to go with him to Las Vegas on his private jet. The boys confront their individual daddy issues