After Alan moves out of the house, Charlie embraces his carefree bachelor lifestyle once again. Alan has a huge fight with his wife Kandi. She plunders all of Alan's money. He is heart-broken to know that Kandi doesn't love him any more. He shows up at Charlie's doorstep with a severe bout of depression. He locks himself up in a room in fetal position. In a desperate effort to pull Alan out of his self-loathin…more
Charlie finally tells Alan why he did not marry Mia and the truth about their relationship. Steven Tyler, Charlie and Alan's noisy neighbor, causes trouble.
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, and takes his words to heart: "Take care of your mother."
After their split, Alan wants to gain custody of his and Kandi s dog.
Alan sets out to get custody of the dog he and Kandi shared as his last grasp for his dignity. Charlie tries to help Jake navigate through a crush.
Jake is upset by Judith's announcement that she is getting remarried. Charlie and Alan try to make friends with Herb to help Jake adjust and to ensure Alan won't have to pay alimony anymore. They give him a bachelor party but accidentally capture incriminating footage on Herb's cell phone.
Charlie's new girlfriend Lydia is a little too much like Evelyn for comfort.
Berta's pregnant daughter shows up at Charlie's to help her mother clean. Berta and Charlie go after the man who got her pregnant.
Alan is having trouble sleeping so he goes for a jog on the beach and the police end up bringing him home. He decides to see a psychiatrist about his sleeping problem and discovers that he has resentment issues toward Charlie. Meanwhile, Jake gets mad at Charlie when Charlie goes out with Jake's friend's mother after he promised Jake he wouldn't.
Charlie and Allan go out on a double date and fight over who's going to pay the check and Jake gets to stay home alone for the first time.
Charlie's girlfriend Lydia fights with Berta and the two tell Charlie he has to choose. Charlie tries to trick them and ends up losing them both. He has to go to Sex Addicts Anonymous to get Berta back. Meanwhile, Allan tries to convince Kandi he needs to sell the condo.
Charlie has plans for a hot date for Christmas Eve, but runs into trouble when instead of getting rid of Alan and Jake, more people keep arriving at his house. When Evelyn discovers who Charlie's date is, she tries to break them up and ends up calling the woman's mother to come help prevent things from going too far. It turns out the woman could be Charlie's sister. Meanwhile, Jake sneaks eggnog and gets drunk…more
Berta is excited when she discovers that Alan has been secretly dating her daughter, Naomi. She starts giving Alan special treatment and arranges for the two families to have dinner together. Alan is saved when Naomi's boyfriend and father of her child shows up at the dinner having made it safely back across the border.
Jake tells Charlie and Alan that he can overhear Judith and Herb having sex and he is worried that you have to be really smart to have sex. The talk triggers a repressed memory for Charlie, and Rose helps him work through it.
Charlie and Berta are having issues with Alan, so Charlie sets Alan up with his new next door neighbor, Danielle. But when things start going well between the two of them, Charlie gets jealous and tries to break them up.
Alan tries an online dating service and falls for the woman he meets until they spend the night together. Meanwhile, Rose tells Charlie of her decision to leave and move to London. Initially Charlie won't believe her, but then when he realizes she's really gone he must deal with his feelings.
Charlie goes with his new young girlfriend to a hot new club and brings Alan along to meet her friend. Charlie and Alan are upset to find out that the young people at the club consider them old.
Evelyn is upset after going to the funeral of one of her friends. No one was mourning at the funeral. Alan and Charlie tell Evelyn if she doesn't change her behavior no one will be mourning at her funeral either. Evelyn invites other people to her birthday to make Charlie and Alan realize that they were wrong.
When Alan sees Jake's covering his walls with posters of women, Alan feels like he needs to get a little more bonding in with Jake while he's still a kid. Meanwhile, Kandi tries to get her career as an actress started.
Alan writes his final alimony check to Judith as she nears her wedding date. Meanwhile, there is trouble at Judith's house as Judith and Herb's sister Myra fight. Charlie invites Myra to stay at his place instead.
Alan gets Jake his tux for the wedding and Jake keeps spilling things on it. Meanwhile, Charlie continues his relationship with Herb's sister despite the objections of Alan and Judith. Alan and Herb's ex-fiance ruin the wedding ceremony and Charlie learns that Myra has a fiance.
Alan befriends Greg, a gay single dad, causing Alan and Charlie to re-examine their own sexual identities. Jake assumes that since Greg is gay, Alan must be too and tells his mother. After everyone keeps congratulating him, Alan begins to think maybe he is gay. Meanwhile, Jake has a crush on Greg's daughter, Sophie.
Instead of helping Jake with his book report like he promised he would, Charlie takes Jake to the track where Jake wins. Alan gives up his good number at the DMV to a pretty woman sitting next to him and gets stuck waiting all day.
Charlie loses a girl to a young, handsome handyman who is working at his house. Even though he wasn't initially interested in the girl, he is upset when the handyman steals her and so he fires the handyman.
When Evelyn's new boyfriend, Teddy, invites Charlie and Alan to a boxing match in Vegas, Charlie is reluctant get to know Teddy. In Vegas, Teddy asks Charlie and Alan they will give their blessing for him to propose to their mother. Initially, Charlie and Alan think he's crazy for wanting to marry her, but they warm up to the idea. When they learn she turned him down, they go and try to convince her to marry him a…more
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