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|colspan="4"| Charlie's life is turned upside down by his brother and nephew moving in with him.
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|colspan="4"| Charlie begins to learn how to parent Jake while Alan attempts to get Judith back.
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|colspan="4"| Alan fears he is losing his son and goes drinking with Charlie.
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|colspan="4"| Alan has trouble with Berta and Charlie needs to get Jake and Rose to follow his suggestions.
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|colspan="4"| After spending a night in Las 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.
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|colspan="4"| Charlie and Evelyn are dating members of the same family.
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|colspan="4"| Judith gets worried when Jake draws the tattooed buttocks of a female surfer friend of Charlie's who walks around his place half naked. Alan feels concern for Judith when she befriends the surfer girl.
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|colspan="4"| Alan tricks Charlie into joining him and Judith in leading Jake and his classmates in the school's annual music show.
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|colspan="4"| Charlie wants to dump a female friend that Jake has grown close to. Alan and Rose bond over a game of scrabble.
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|colspan="4"| In an attempt to prove that he is a family man, Charlie invites Lisa over for Thanksgiving dinner
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|colspan="4"| 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.
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|colspan="4"| When Berta is forced to bring her granddaughter Prudence to work with her, the boys find themselves a little preoccupied with her.
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|colspan="4"| 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.
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|colspan="4"| Stan, Charlie's accountant, tries to explain Charlie's financial woes to him.
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|colspan="4"| Against Alan's judgment, Charlie falls for a seemingly crazy woman named Frankie.
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|colspan="4"| Frankie tells Charlie and Alan why she and her daughter are on the run; Frankie's daughter has a crush on Jake.
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|colspan="4"| Alan offends Charlie by choosing harebrained cousins as Jake's guardians in the event of his death.
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|colspan="4"| Charlie is stunned to learn his ex-girlfriend is now a man.
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|colspan="4"| Judith's sister, Liz, hits on Alan at Jake's birthday party; Evelyn prefers alcohol to cake.
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|colspan="4"| 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.
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|colspan="4"| Charlie jeopardizes Alan's divorce settlement by sleeping with his attorney, Laura.
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|colspan="4"| Charlie attempts to cure Alan of his recent bout of sleepwalking; Jake sees his therapist.
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|colspan="4"| Charlie tries to sweet talk Judith's divorcee support-group into letting Jake continue to spend weekends at his place.
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|colspan="4"| A pregnancy scare has Charlie heading to the doctor for a vasectomy.
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|colspan="4"| Alan learns that Charlie belongs to an exclusive men's group, and he begs his brother to let him join.
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|colspan="4"| Judith is dating Jake's pediatrician, and Alan is upset until Charlie points out that if she remarries, his alimony payments will end.
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|colspan="4"| Charlie tries to save Jake from school suspension for giving his teacher (Missi Pyle) the finger by romancing her, but his attempts fail every time.
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|colspan="4"| Jake is very impressed and can't stop talking about his mother's new boyfriend, Dr. Melnick, which annoys Alan. Evelyn borrows Charlie's car to help her impress a Saudi prince, she is trying to sell a house to, but when Charlie gets his car back, he discovers his mother's bra in the backseat.
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|colspan="4"| Charlie meets his match when he falls for a woman who's better at playing hard to get than he is.
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|colspan="4"| 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.
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|colspan="4"| Charlie and Alan hire Berta's sister to cater a party their mother has conned them into throwing for her.
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|colspan="4"| 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.
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|colspan="4"| 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.
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|colspan="4"| 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.
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|colspan="4"| 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.
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|colspan="4"| Alan is jealous of Charlie when an old classmate, who's now a beautiful woman, seems to be more interested in Charlie.
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|colspan="4"| 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.
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|colspan="4"| 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.
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|colspan="4"| 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.
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|colspan="4"| 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 than Alan.
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|colspan="4"| After Charlie has back pain, Alan decides to take him to the Hospital after refusing alan's help. 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.
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|colspan="4"| 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.
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|colspan="4"| 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.
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|colspan="4"| Rose tries to help the brothers sort out their feelings, when Charlie and Alan take their personal frustrations out on each other.
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|colspan="4"| 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.
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|colspan="4"| 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.
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|colspan="4"| 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, Alan 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.
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|colspan="4"| Charlie unknowingly sleeps with an older man's trophy wife while Jake has to read a paper to his class.
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|colspan="4"| After falling off the roof, Alan needs someone to watch Jake and Charlie offers, until, it interferes with his social life.
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|colspan="4"| 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.
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|colspan="4"| Charlie, finds out that Alan and Judith have begun to date again.
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|colspan="4"| Berta causes tension between Charlie and Alan, when she temporarily moves in with them.
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|colspan="4"| Charlie learns he can't be in a long-lasting relationship because of unresolved issues he has with his mother. Jake asks Charlie for advice about a girl at school.
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|colspan="4"| Ignoring Alan's warnings, Charlie continues to date Isabella until she threatens to put a curse on his manhood.
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|colspan="4"| 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.
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|colspan="4"| Charlie tricks Jake into taking ballet lessons, so he can get close to the teacher.
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|colspan="4"| One of Charlie's elderly neighbors tries to seduce Alan, while Charlie tries to stop Jake from giving money to a televangelist.
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|colspan="4"| Charlie helps Alan with his obsession of always having to get approval from the women in his life.
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|colspan="4"| Alan starts dating a woman with a Martha Stewart complex. Before long she's running the house with an obsession for perfection.
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|colspan="4"| Charlie sees a therapist to learn how to deal with Alan's emotional insecurities.
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|colspan="4"| Charlie finds himself in a relationship that is not based on sex.
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|colspan="4"| Charlie arranges a romantic date with Mia in the hopes of consummating their relationship. Alan begins to date Charlie's most recent ex-girlfriend.
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|colspan="4"| 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.
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|colspan="4"| Alan has trouble deciding if he should bring his younger girlfriend to Jake's birthday party to meet his mom and his ex-wife. Rose tries to get her boyfriend to act more like Charlie.
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|colspan="4"| 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.
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|colspan="4"| 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.
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|colspan="4"| Charlie is surprised to find out that Kandi has been living with them for the last three weeks. Alan is having a tough time helping Kandi earn a living. Charlie has lost his sense because of the dry-spell he is going through.
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|colspan="4"| Alan tries to win Kandi back. Meanwhile, Charlie starts to sleep with her mom, Mandi, and Judith gets set up with her father, Andy.
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|colspan="4"| Jake’s teacher has a meeting with Alan and Judith to discuss the lack of interest Jake has at school. Alan starts to fall for Francine, in a platonic way, because he is tired of the lack of intelligent communication he has with Kandi. Charlie helps Jake audition for his school musical.
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|colspan="4"| A girl from Jake’s school invites him to his first boy-girl party. Charlie and Alan help him get ready for it by giving him advice. Alan and Charlie get nostalgic and remember their first boy-girl party.
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|colspan="4"| Mia comes back to town with her dance troupe and invites Charlie to her performance. At first, he decides not to go and tries to convince Alan that he no longer has feelings for her. He goes to the see the performance and Mia explains that she wants some of Charlie’s sperm. Charlie responds by asking Mia for something.
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|colspan="4"| Charlie and Mia start making their wedding arrangements. Things begin to fall apart when their two families meet each other. They eventually decide on a small ceremony in Las Vegas.
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|colspan="4"| Charlie returns to his bachelor lifestyle after Alan moves out of the house. Alan suffers a break down after his divorce from Kandi.
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|colspan="4"| Charlie finally tells Alan the truth about why he did not marry Mia. Charlie and Alan deal with a noisy neighbour.
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|colspan="4"| 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.
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|colspan="4"| Alan tries to hire his ex-wife's lawyer to help him win custody over the dog he and Kandi shared.
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|colspan="4"| 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.
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|colspan="4"| Charlie is dating a woman whose personality and life are like his mother’s.
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|colspan="4"| Berta's daughter, Naomi is pregnant and Berta drags Charlie with her when she confronts the baby’s father. Alan reveals a secret fetish.
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|colspan="4"| Alan suffers from insomnia. He visits his psychiatrist [[Jane Lynch]], who reveals that the cause of Alan's sleepless nights is his jealousy towards Charlie, and his inability to glide through life.
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|colspan="4"| 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.
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|colspan="4"| 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.
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|colspan="4"| 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.
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|colspan="4"|Alan becomes involved with Berta's daughter Naomi, who has a newborn daughter of her own. This causes Evelyn to tell Alan during dinner with both families that she disowns him, until Naomi's boyfriend suddenly arrives, forcing Alan and Naomi to break it off.
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|colspan="4"|Charlie's mother, Evelyn, puts his house on the market without asking him, showing it to a wealthy, elderly Japanese man named Hiroshi. Charlie later catches Evelyn and Hiroshi naked in her living room together behind the couch.
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|colspan="4"|Charlie sets Alan up with their new neighbour. But he gets jealous when the two form a bond.
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|colspan="4"|Rose is moving to London, and Charlie is surprised by his reaction to the news. Alan lies to a woman he met online.
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|colspan="4"|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".
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