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.

Jake is very impressed and can't stop talking about his mother's new boyfriend, Dr. Melnick, which annoys Alan. While Evelyn borrows Charlie's car to help her impress a Saudi prince, because she wants to sell him real estate. When Charlie gets his car back, he discovers his mother's bra in the backseat. When he finds out why it's there he decides to trade in his car.

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

Alan denies having shoplifted a toy as a child and fears he has a dark side, until Charlie admits he planted the toy on Alan to stay out of trouble himself.

Charlie and Alan hire Berta's sister to cater a party their mother has conned them into throwing for her.

Alan meets a woman named Nancy at a grocery store, who fulfills every single one of his desires, forcing Charlie to take care of Jake. After knowing Nancy for a few days Alan decides to ask her to marry him, prompting Charlie to try and talk him out of it, and he even gets help from the brothers' mother.

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.

Charlie tries to get Jake's approval on a theme song that he is hired to write for a television show, which is based on a comic book that Jake is a fan. While Alan finds out more about Rose (including how smart she is), when he spends more time with her.

After getting unusually turned down at a bar, Charlie learns that a website has been made dedicated to exposing his lifestyle. Charlie sets out to find who created the site, making amends to all those he stood up, but it's harder than it looks when all the women take the apology better than expected.

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

After an earthquake hits, Judith's house is damaged and she needs a place to stay. So Alan decides to invite her to stay with him and Charlie, without getting Charlie's permission. Charlie isn't happy with this, but accepts it. Alan becomes jealous when Judith goes on a date, and asks Charlie to find him a date, so that he can show Judith that he dates as well.

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.

When Judith decides to take a vacation, the brothers have to take care of Jake during the week. Alan finds it challenging, and even forgets to pick up Jake from soccer practice. When Alan finds out that he has to go to the I.R.S. because they're auditing him, he forces Charlie to take care of Jake, and Charlie doesn't do any better then Alan.

After Charlie has back pain, Alan decides to take him to the Hospital. While there Charlie can't stop hitting on the doctor who is examining him. The only problem is that he has a history with her that he can't remember. Berta is feed up with Jake's inability to use the bathroom properly, so she decides to make him clean it until he learns.

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.

After Charlie takes Alan to an eye doctor, they end up at cafe where they bump into Charlie's ex-girlfriend, Sherri. While there Alan shows an interest in Sherri, and decides to ask her out. The problem is that Alan can't get over Sherri's relationship with Charlie.

Rose tries to help the brothers sort out their feelings, when Charlie and Alan take their personal frustrations out on each other.

Evelyn reads in the obituaries that her second husband, Harry has died. They all attend the funeral, including Jake who is excited at the opportunity of seeing a ""dead guy"". Charlie is excited by the opportunity of a newly single widow, and Alan is just happy to pay his respects to Harry.

Evelyn buys Alan a new Sports car causing Charlie to claim that his brother has sold his soul to the Devil. The next day, Evelyn extracts payment by insisting that Alan go on a blind, double date with her, her new beau and his daughter. At the restaurant, Alan learns that his mother and boyfriend will not be able to join them because there was a mixup between his heart medication and Viagra and she didn't want to ""waste it"". As a result, Alan is left to deal with the daughter, who is on a weekend pass from a rehab center and still has some loose screws. Alan eventually gets her back to the beach house only to have her drive off in his new sports car and become the object of a televised high-speed car chase.

Evelyn demands Jake spend a night at her place when she finds out he spent Spring Break with Judith's parents. Neither Alan nor Charlie are keen on the idea, but going to a bar after dropping off Jake quickly erases their concerns.

Charlie unknowingly sleeps with an older man's trophy wife while Jake has to read a paper to his class.

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

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.

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

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.

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

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

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 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.

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.

Berta discovers that Alan has been dating her daughter Naomi.

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.

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

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

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".

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.

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

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

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

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

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

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.

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 is getting ready to start a new school as he graduates to Junior High. Alan and Charlie take him school shopping and find themselves in trouble.

Charlie acts strange after spending an evening with his mother, and a woman Alan slept with behaves oddly the next morning.

Alan convinces Charlie that he needs to date more respectable women and sets him up with a judge. The two double date and their waitress happens to be one of Charlie’s ex-girlfriends. Charlie's date backfires the following morning, when he ends up in court in front of the judge.

Charlie and Linda get closer to consummating their relationship, but Charlie has trouble focusing when he begins to see Rose's face everywhere he turns.

Charlie has to come up with ways to keep his girlfriend's 4-year-old amused; Alan becomes a test subject.

Charlie's girlfriend is embrassed to go out in public with him. Meanwhile, Jake sneaks out to attend a concert.

After Alan and Charlie have a fight about Alan's role in the house. Alan packs Jake up and moves in with his mother.

Charlie writes a children’s song and finds success as Charlie Waffles. The children love him and the mothers seem to as well. Charlie's new found fame irritates Alan.

Charlie fights his attraction for Teddy's daughter.

Alan finds out that Charlie stole his girlfriend and works on a plan to get back at Charlie, even though this happened when they were in high school.

When Alan finds himself wanting to break up with a woman, Charlie offers his expertise.

Rose returns from England, and plays nurse rather oddly for an ill Charlie.

Alan finds out some surprising information about Judith's sex life when he decides to go on a date with one of her friends.

Charlie double-dates with Jake and fixes Alan up with a hooker.

Alan feels Charlie is unable to control his womanizing ways.

Alan makes wedding plans for Evelyn and Teddy, while Charlie figures out how to get more acquainted with his future step-sister.

CSIs investigate a death at Charlie's house.

Charlie's attracted to an older self-help author. Alan and Jake clash over a project for school.

When Charlie meets Angie's soon to be daughter-in-law, he realizes it's not for the first time.