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Alan learns that Charlie belongs to an exclusive men’s group, and he begs his brother to let him join. When Charlie doesn’t, Alan tries to contact his old friends, but discovers that Judith befriended them and turned almost all of them against him. Eventually, Charlie lets Alan in to his group, but Alan begins to irritate everyone and ends up getting himself tied to a streetlamp. Guest stars Elvis Costello, Sean Penn, Bobby Cooper and Harry Dean Stanton as themselves, who are part of Charlie’s exclusive group.

Judith is dating Jake’s pediatrician, Greg (Ryan Stiles), and Alan is upset at the thought of Judith being with another man – until Charlie points out that if she remarries, his alimony payments will end, so Alan attempts to befriend him. While giving Greg a massage, Judith walks in on them, and Alan snaps Greg’s neck accidentally in panic – causing him to pay more money than he had to in the first place.

When Jake gets in trouble at school for giving his teacher, Delores Pasternak (Missi Pyle), the finger, Charlie decides to woo her as an attempt of saving Jake from being suspended. Jake then catches the two in the middle of the night. When Alan finds out, he insists that Charlie break it off, but later insists that Charlie not because Jake has been getting great grades on his papers. Charlie breaks it off with Delores, anyway, due to the fact she wants a commitment, and she punishes Jake by giving him double the amount of his regular homework.

Jake is very impressed with his mother’s new boyfriend, Greg, after Greg teaches him various activities which annoys Alan. Meanwhile, Evelyn borrows Charlie’s car to help her impress a Saudi prince she’s trying to sell a house to and lends Charlie her electric car. Alan and Charlie then teach Jake how to drive in this car. Judith breaks up with Greg and Alan is there to support her; the two begin to have sex until Jake and Charlie walk in on them, but Jake doesn’t believe Charlie when he explains that Alan and Judith were about to sleep together.

Charlie meets his match when he falls for a woman (Sherri, played by Jeri Ryan) who’s better at playing hard to get than he is. After repeatedly using him for sex, Charlie tries to get revenge on Sherri, but ends up punishing himself too. Meanwhile, Alan has a hard time teaching Jake to do his homework, and Jake is upset at the fact Charlie keeps eating all of his food.

While out at a family meal, Evelyn lets out a secret of Alan’s past – he shop lifted when he was younger. 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. Alan finds it impossible to forgive Charlie until Evelyn asks Alan to move in with her because of Alan’s dislike towards his brother.

Charlie and Alan end up having to throw a party for Evelyn at the house. Berta hires her sister, Daisy (Camryn Manheim), to help out with the planning, but the two can’t stop bickering. Eventually, Charlie has a talk with Daisy, and she agrees to help out. However, this backfires when the guests of the party focus on her singing rather than Evelyn. Evelyn then begins moaning at Alan and Charlie, as does Judith when she thinks they taught Jake to be sarcastic towards her.

Alan meets a woman named Nancy at a grocery store, who fulfils every single one of his desires, forcing Charlie to take care of Jake. After only knowing Nancy for a few days Alan decides to ask her to marry him, prompting Charlie to try to talk him out of it, and he even gets help from the brothers’ mother. Alan calls Nancy to propose to her, but she then tells him that her husband has returned from his vacation trip early—causing her relationship with Alan to terminate.

When Charlie leaves the house to avoid a date that he can’t stand, he ends up at a coffee shop, where he reconnects with his old girlfriend Lisa (Denise Richards), now a divorcée with a child. Meanwhile, Alan walks in on Charlie’s date in the shower and she frighteningly attacks him and Jake uses this situation to blackmail Alan; Jake tries numerous excuses to justify why he is getting bad grades.

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 of which Jake is a fan. But Jake doesn’t like Charlie’s idea and the two write a new song instead. Meanwhile, Alan and Rose begin to spend time together and eventually share a kiss; they later decide to remain just friends.

After getting unusually turned down at a bar, Charlie learns from Jake 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 (including, amongst others, Jennifer Bini Taylor), but the website is still standing. It isn’t until Charlie apologies to Rose that the website is fully shut down. Meanwhile, Alan thinks that Judith wants to get back with him after hearing her talk to her mother on Jake’s webcam.

Alan is jealous of Charlie when an old classmate, Jamie Eckelberry (Paget Brewster), who’s now a beautiful woman, seems to be more interested in Charlie, before it is revealed that she hates him and worked hard to make herself a beautiful woman to rub his nose in it. She reveals that she used to be interested in Alan when they were younger, but shoots him down after he asks if they could try to go back to that now.

Alan invites Judith to stay at Charlie’s place after an earthquake severely damages the plumbing in her house. When Judith goes out on a date, Alan becomes extremely jealous and somehow ends up letting Judith throw him out of Charlie’s house. Charlie then sets Alan up with a beautiful woman he knows, which makes Judith jealous and leave the house.

Alan and Charlie help Jake study for a History test which he passes. When Evelyn manages to make this into a bad thing and sucks the self-esteem out of Jake, Alan furiously throws her out and tells her she can’t see her grandson. Later, Alan receives a call that Evelyn has been taken to hospital. He and Charlie realize that it’s fake and pretend to go along with it by suggesting surgery. However, when she goes along with the ruse, it makes Charlie and Alan’s efforts to expose her futile. The episode ends with Evelyn shown to be temporarily living with Charlie and Alan after the surgery.

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. Berta overhears this and invites her friends over for a party. However, Jake becomes ill beforehand and then tells Judith everything on the phone. A furious Judith then comes over to scold the two, but Charlie and Alan decide to go anyway until Jake becomes ill again (causing Alan to realize he’s going to face it sooner or later). Charlie and Alan then head downstairs after putting Jake to bed to find Berta hosting a party.

When Judith decides to take a vacation, Alan has to take care of Jake during the week. After a hard day at work, Alan forgets to pick Jake up from school, and then finds out that he has an important meeting at work the next day, meaning Charlie has to look after Jake. Charlie then forgets to pick Jake up from school as well.

After Charlie has back pain, he refuses to accept help from Alan, who decides to take him to the hospital, where he keeps hitting on his doctor (Alicia Coppola), unaware that he has dated her before. Meanwhile, Berta is fed up with Jake’s inability to use the bathroom properly, and gives him a day of cleaning.

Charlie is invited to a party hosted by a gay ad-executive named Eric (David Starzyk), so Charlie asks Alan to pretend that he is his life partner. Charlie then meets Eric’s gorgeous ex-wife (Lucy Lawless) who doesn’t believe him when he claims he is straight. Charlie then returns home to find out that Eric had tried to hit on Alan.

After Charlie injures Alan by throwing toast at him, he takes Alan to an eye doctor; they later end up at the coffee shop where they bump into Charlie’s ex-girlfriend, Sherri (previously seen in "Bad News from the Clinic"). 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, causing her to angrily break up with him.

Evelyn rings the house phone, and Charlie answers. Evelyn frustrates him in a matter of minutes. Meanwhile, Alan answers the door to Judith, who ends up frustrating him. Alan and Charlie then take their problems out on each other. The next day, they reconcile, until Charlie finds out that Berta threw out his expensive clothes. Rose steps in to resolve the issue, and they spend the afternoon discussing Charlie and Alan’s problems with 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 tells her sons a secret: her husband had cheated on her, and she still loved him; it turns out that her husband then cheated on the girl with whom he cheated on Evelyn.

Alan gets a new sports car which everyone claims is a woman’s car. When asked where he got the money, Alan claims he "found it," until finally telling Charlie that his mother lent him the money. Charlie warns that she’ll want pay back, and sure enough she asks Alan to go on a double-date with her. She then doesn’t show up, leaving Alan with his recovering alcoholic date, Trudy (Chloe Webb). After she passes out, he takes her home and leaves her in his car, but accidentally leaves the keys in the car and the garage door open. Trudy is then seen on the news driving his car down a freeway at high speed.

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 when a group of attractive women show up. Evelyn tries to get Jake to eat sushi and squab, which Jake doesn’t like. She then makes him spaghetti, which she throws over him after he scares her, making her jump. Jake then takes a bath but leaves the tap on, causing the ceiling to break and the wave of water to come crashing down on Evelyn. Alan and Charlie then decide that Jake is "the chosen one" because he "broke her" (Evelyn).

Jake has to read a report of his weekend to his class. In the report, it is revealed that Charlie slept with an older man’s (Norman) wife, who then came to the house to seek revenge on Charlie. Charlie and Norman eventually talk things out, and Norman becomes attracted to Evelyn when she shows up. Evelyn tells Berta, Alan, Charlie and Jake to go and see a movie. When they return, they walk in on Evelyn and Norman having sex. Meanwhile, Jake is oblivious to everything around him (even Norman’s wife sneaking out of the house) because he has lost his Game Boy and can’t find it. He eventually finds it when taking a pee in the plants. Orson Bean guest stars as Norman, the older man whose wife had slept with Charlie.