After Charlie's night with a girl is ruined due to Alan's interuption, Alan moves in, being kicked out of his house by his "suffocated" wife: Judith. The next day Alan brings over his son, Jake while he and Judith can talk about their marraige. While eatting, Alan finds out that Judith is a lesbian therefore their relationship ends. Charlie takes to Jake, and begins to take him shopping to meet girls and lets him play at his poker games. Upset, Alan moves in with their mother, Evelyn, taking Jake with him. Charlie now feels surprisingly empty and invites Alan and Jake to move back in, convincing Alan that all their problems in life are because of their controlling mother and that Jake would only end up being just as messed up in later life.
While spending time with Jake, Charlie finds it hard to enforce rules that Alan has set out for him. It gets to the point were Jake lures a folk of sea gulls into his room, and Charlie gets very upset. This prompts Jake to try and get Charlie to forgive him. Alan starts doing chores for Judith, in the hopes of them getting back together. During one of the tasks, Judith kisses Alan, leading him to believe that things will get back to the way they once were.
Go East on Sunset Until You Reach the Gates of Hell
After spending a day at Disneyland, Jake gets sick and wants to go to his mothers' house, to have her take care of him. This sends Alan into a state of misery, as he realizes he's losing his wife, and son. Charlie suggests that they go drinking, and Alan agrees. After drinking the boys take a cab home, but at one point they end up at their mothers, where they try to tell her what they think of her, but fail in getting the point across.
If I Can't Write My Chocolate Song I'm Going to Take a Nap
Charlie is very unhappy with his housekeepers' decision to quiet, after she experiences Alans demanding ways. Alan then offers to take on the role of housekeeper, but this situation doesn't work at all. So Alan decides to get the housekeeper to come back. Before Alan leaves, he puts Charlie in charge of getting Jake ready for a dinner with his mother and grandparents. Charlie also tries to get Rose to move on, and date other men. He finds both situations to be bigger challenges then he first thought.
After spending a night in Los Vegas, Charlie decides to live up to his promise that he made to Jake about attending his soccer game. During the game, Charlie sets up a play-date with an unattached mother named Kate, and they hit it off. During one of their dates, Charlie seems like he's ready for a serious relation. Alan sets up a meeting with Gloria (one of the soccer moms) to write a soccer newsletter, but Gloria has other intentions for the evening, and he has no idea. During the evening another soccer mom, Brooke, tries to move in on Gloria's plans.
Did You Check With the Captain of the Flying Monkeys?
Charlie tries to teach Jake to avoid certain calls that Charlie doesn't want to deal with, like his mother (Evelyn) for one. Evelyn gets so frustrated with not being able to talk to Charlie, that she decides to drop in while in the neighbourhood. She invites them to dinner, to meet her new boyfriend (Tommy). When the brothers get over to their mothers house, Charlie is shocked to realize that Tommy's daughter is Olivia, one of the people he has been avoiding. Olivia tries to confront Charlie about their situation, but doesn't get the answer she wants, and throughs her drink in his face, then storms off. After a week of not being able to contact their mother, Alan gets worried about her. So the brothers decide to go to her house and see if she's okay. They find her sitting in the dark and drinking, and she informs them that Tommy dumped her for a younger women. Later the brothers get Jake to try and cheer her up.
Judith gets worried when, for a school assignment, Jake draws the tattooed buttocks of a female surfer friend of Charlie's who is in the habit of walking around his place half naked. Then Alan gets worried about Judith after she becomes friends with the surfer girl.
After meeting Wendy, a one-night stand of Charlies, Jake befriends her. Charlie doesn't like this situation, as he believes Wendy is using Jake to further their relationship, and he has no intention to keep it going. It gets to the point were Wendy even starts spending time with Evelyn, and Charlie becomes desperate to get rid of Wendy. After Charlie breaks it off Jake becomes very unhappy with him, because he won't be able to see Wendy anymore. This forces Charlie to confront Jake and explain the situation as best as he can. Rose sees that Alan knows how to play scrabble, and asks him to teach her to play, he agrees. During the scrabble games the two bond, and Charlie suspects that she is using Alan to get closer to him, but doesn't pursue the issue.
While at the movies, the brothers bump into Judith and her new boyfriend. Seeing that Judith has changed her look, and the fact that Jake doesn't think Alan is as cool as Judith; prompts Alan to realize that if he wants to get back into the dating scene, he's going to have to change his look as well.
Charlie finally gets a chance for a double date with a hot neighbor, who is out for revenge on her cheating husband, and her sister who's a hot soap opera actress, and needs Alan to come along. The problem is that Alan gets sick from Jake, so Charlie takes them to a steam room to help Alan get rid of his flu symptoms. This backfires, as Charlie also gets sick, but he has no intentions of canceling the date.
Judith believes that Jake is having a hard time dealing with his parent's divorce, after he starts annoying everyone with his non-stop guitar playing. So she suggests that they send Jake to a therapist. Alan doesn't agree at first, but after thinking about it, he believes it might not be such a bad idea.
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.
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.
After an earthquake hits, Judith's house is damage 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.
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 their 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.
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.
When Evelyn learns that Jake spent his entire spring break with his grandparents, she pressures Alen into letting Jake stay with her for the night. Conserned that Evelyn will destroy Jake the way she destroyed their lives, Alen and Charlie grudgingly drop a resentful Jake off at her home and quickly flee to Charlie's favourite bar. There, amidst a group of sexy women, Alan easily gets his mind off of his son's miserable circumstance.
Jake gets suspended from school after drawing an offensive picture of a girl in his class that has large breasts. Meanwhile, Charlie is asked to watch over Alan's chiropractic office after pulling an all-nighter.
Charlie finds out that Alan hasn't been dating other women, but infact has been seeing is ex-wife. To keep Jake from finding out, Alan tells Charlie not to tell him because he doesn't want Jake to get his hopes up. Charlie then tries everything he can to convice Alan to come to his senses because he knows it will only end bad for him. But later he tells Rose that if Alan gets back together with his ex-wife, he won't get to see Jake as much. Meanwhile, Alan takes a book back for jake but while at the house Judith offers Alan to join her for a drink in the hot-tub, but it doesn't go so well when Jake keeps interrupting. They then take it to the bedroom, but as usual, Alan screws things up for himself.
Charlie wakes up with Rose the morning after her birthday party. Her irate father (Martin Sheen), comes to ask Charlie about what the future holds for him and Rose, but the unexpected happens when Evelyn shows up.
Charlie has trouble keeping up with Mia's healthy lifestyle, so he begins to sneak beers, cigars, and burgers behind her back. When Mia finds out what he was doing, Charlie has to decide if he is truly in love with her or just whipped.
Charlie is nominated for an advertising award, but he decides to boycott it because his arch nemesis always wins. The rest of his family tries to trick him into going. Rose is having relationship problems with Gordon and seeks help from Charlie.
Alan starts to have financial problems when he starts paying for his girlfriend's bills, so Charlie tries to get him to break up with her. Meanwhile, Judith is after Alan because he is late in paying his alimony check.
Charlie finally tells Alan the truth about why he broke up with Mia, and a famous neighbor causes problems. Alan feels guilty when he learns that Charlie and Mia didn't tie the knot because she had wanted him and Jake to move out. Meanwhile, Charlie and his rock star neighbor don't get along.
After nearly drowning, Charlie is convinced he saw his late father. Charlie attempts surfing in order to impress a beautiful girl -- with disastrous results. He later tells Alan that when his life was hanging in the balance, their deceased father came to him and made a request that Charlie's loath to fulfill.
Alan and Kandi become embroiled in an unconventional custody battle. Alan is determined to gain custody of his and Kandi's dog after she walks away from their split with both the condo and the car. Having also lost everything to Judith following their divorce, Alan decides to hire the best lawyer he knows -- hers.
Alan and Charlie bond with Judith's new fianc in an effort to improve his relationship with Jake. Alan is overjoyed that he'll no longer owe Judith alimony when she marries Herb. When their marriage plans are threatened due to Jake's disdain for his soon-to-be stepfather, Alan enlists Charlie's help to keep Herb from getting cold feet.
Charlie cannot see that he's dating a younger version of his mother. Though Charlie despises his sharp tongued, passive aggressive mother, he's strangely attracted to Lydia, an attractive, blonde high-end real estate agent -- just like his mother. Unfortunately, the similarities don't end there, and the relationship begins to seem a little too familiar for comfort.