Charlie's life gets a little more complicated when his brother, Alan, and son, Jake, move in with him after his wife confesses her lesbian lifestyle and throws him out of the house. Alan later leaves after finding his son playing poker and moves in with his mother, Evelyn. Charlie realizes how lonely it is without them and invites them back.
Charlie finds it hard to enforce the rules Alan has set out for his son. After Jake lures a flock of sea gulls into his room, Charlie gets very upset. Jake tries to get Charlie to forgive him. Alan starts doing chores and errands for Judith, trying to get them back together. After one of his tasks, she kisses him, leading him to believe that things will be back to normal.
After a trip to Disneyland, Jake gets sick and wants to go to Judith's house so she can take care of him. Alan gets saddened over this because he is losing his wife and son. Charlie takes him to a bar, and after drinking, they end up at their mother's house trying to tell her what they think of her, but not successful in the process.
Berta, the housekeeper, quits after experiencing Alan's demanding ways. Alan decides he could be the housekeeper, but does not work. Alan decides to hunt her down and bring her back, leaving Charlie to get ready for dinner with his mother and grandparents. Charlie also tries to get Rose to date other guys, both tasks become harder than expected.
After a trip to Las Vegas Charlie decides to go to Jake's soccer game like he promised. There, he meets a soccer mom and they hit it off. Alan goes to a meeting with some soccer moms about creating a newsletter, but does not realize they have other plans for the night.
Charlie gets in over his head after he tells Jake to avoid certain calls he doesn't want which creates a dinner plan for Charlie and his mother. When Charlie meets her new boyfriend's daughter, he realizes it is one of the people he is trying to avoid.
For a class assignment, Jake draws the tattooed buttocks of one of Charlie's surfer friends, which in turn, worries his mother. Alan then starts to get worried about Judith when she becomes friends with the surfer girl.
Alan tricks Charlie in leading Jake and his classmates in the music show along with Alan and Judith.
Jake befriends one of Charlie's one-night stands, which Charlie does not like as it furthers the relationship that Charlie does not want to continue.
To try and prove to his girlfriend that he is a family man, Charlie invites Lisa over for Thanksgiving dinner at his house.
After bumping into Judith and her new boyfriend at the movies, Alan decides to change his look to try and get back into the dating scene, and to impress his son.
Berta becomes forced to bring her granddaughter Prudence to work for a day. The boys like this because they get very preoccupied with her.
Charlie gets a double date with a hot neighbor and her sister and needs to take Alan along. The trouble is, Alan got sick from Jake so Charlie takes him to a steam room to heal him. It works for Alan, but Charlie becomes ill, but won't cancel the date at any cost.
Charlie's accountant Stan tries to explain Charlie's financial problems to him.
Charlie falls for a seemingly crazy woman named Franky against Alan's constant arguments about the woman.
Frankie tells Charlie and Alan why both her and her daughter are on the run, and Frankie's daughter gets a crush on Jake.
Charlie gets offended after Alan chooses harebrained cousins as Jake's legal guardians in the event of his death.
Charlie is stunned to find out that one of his ex-girlfriends had a sex change operation.
At Jake's birthday party Judith's sister Liz hits on Alan while Evelyn prefers to drink alcohol than eat cake.
When Jake starts playing guitar non-stop, Judith thinks it is because he is having a hard time dealing with the divorce. She suggests that he sees a therapist, which Alan does not agree with at the beginning, but agrees later on.
Charlie puts Alan's divorce settlement into jeopardy when he sleeps with his attorney, Laura.
Charlie tries to cure Alan of his recent sleepwalking adventures; Jake goes and sees a therapist.
Charlie uses his silver tongue on Judith's support group to convince Judith into letting Jake still spend weekends at his place.
Charlie heads to the doctor for a vasectomy after a recent pregnancy scare.
Alan begs Charlie to include him in his exclusive men's group.
Alan gets upset when he finds out Judith is dating Jake's pediatrician. Charlie points out, however, if she does marry him that Alan's alimony payments will end.
Jake is on the verge of getting suspended from school when he gives his teacher Miss Pyle the finger. Charlie tries to save Jake from the suspension by dating her, but fails several times.
Jake loves his mother's new boyfriend Greg and won't stop talking about him, which bugs Alan. Evelyn borrows Charlie's car to impress a Saudi prince, so she can sell him real estate. When Charlie gets his car back, his mother's bra is found in the backseat. After he finds out why it is there, he trades it in.
Charlie meets somebody who can play hard to get better than he does, which makes him want her even more.
Alan denies ever shoplifting a toy as a child and fears that he he might have a dark side to him. Charlie admits that he planted it so he wouldn't get in trouble from their mom.
Charlie and Alan hire Berta's sister to help set up and cater a party that their mother had talked them into throwing her.
Alan meets the girl of his dreams in Nancy, who fulfills all of his desires which forces Charlie to take care of Jake. Trouble stirs a few days later when Alan decides he wants to marry her.
Charlie leaves a date he can't stand and ends up at a coffee shop where he runs into his ex-girlfriend, Lisa. She has broken up with her husband and left with a child. He tries to convince her that he's okay with her having a child. Jake tries to reason with his father why he isn't doing too well in school.
Jake helps Charlie come up with the theme song for a children's television show which is based on one of Jake's favorite comic books. Alan finds out how smart and fun Rose is when he starts spending more time with her.
Charlie finds out about a website created by him that shows how evil he is to women. Charlie goes and tries to find out who made the site by apologizing to all of them. He finds it hard to track down the creator when all the women take the apology a lot better than he expects.
Alan gets jealous when an old classmate who grew up to be a beautiful woman seems more interested in dating Charlie then himself.
Judith's house (actually Alan's of course) gets damaged during an earthquake and needs a place to stay. Alan offers Charlie's house without his permission. Charlie agrees, although not happy at first. Alan gets jealous when she goes on a date and has Charlie find him one to show her he can date just like anyone else.
After insulting the way Alan raises Jake, Alan and Charlie throw Evelyn out of the house. After ignoring her numerous phone calls, she feigns an emergency at the hospital which Aland and Charlie believe at first, until they catch her bluff.
Alan gets worried about a minor medical procedure he is going to face, so Charlie decides to take him to Vegas to get his mind off it.
Alan and Charlie have to take care of Jake the whole week while Judith takes a vacation, which proves harder then they imagined.
Alan takes Charlie to the hospital where he hits on a doctor he didn't know he had past history with. Berta is fed up with the way Jake uses the bathroom so she makes him clean it until he learns.
Charlie is invited to a party hosted by a gay ad-executive named Eric and he takes Alan pretending they are life partners. While there, Charlie meets Eric's ex-wife Pamela, and tries to get with her without Eric knowing.
After Charlie takes Alan to the eye doctor they end up at a cafe where they both bump into Charlie's ex-girlfriend, Sherri. Alan deicdes to ask her out after showing interest, but he can't get over the relationship she had with Charlie.
When Charlie and Alan take their personal frustrations out on each other, Rose buts in the middle to try and help them out.
Evelyn reads that her second husband Harry had died. They all attend the funeral. Jake is excited to see a "dead guy" while Charlie is excited about the opportunity of a newly single widow, and Alan is glad he can pay his respects to Harry.
After his mother buys him a new sports car, Alan discovers the gift has strings, specifically the crazy daughter of her new boyfriend.
After learning that Jake spent his whole Spring Break at his other grandparents, Evelyn pressures Alan to have Jack spend more time with her. Alan is worried she will screw him up, like she did to him and Charlie. He agrees, though, and drops him off at her house. Alan meets a sexy woman at Charlie's favorite bar, which easily gets his mind off his son's bad time.
Jake must read what he did over the weekend as an essay to the class. The weekend consists of Charlie unknowingly sleeping with an elderly man's trophy wife over the weekend.
After Alan falls off a ladder, Charlie ends up watching over him and Jake, which proves to be a harder task than he thought.
Jake gets suspended from school after he draws a picture of a girl in his class with huge breasts. Charlie is asked to watch over Alan's chiropractic office after pulling an all-nighter, while telling Charlie not to do anything but answer the phone. Charlie turns the place into a get rich quick scheme.
Alan's dating dry spell turns out to be because he has been seeing his ex-wife on the sly.
When Berta moves in temporarily, Alan and Jake move out because of her.
Charlie has trouble committing to a relationship and decides it is because of his issues with his mother.
Alan disapproves of Charlie's latest girl, and the feeling is mutual.
Charlie is shocked when he wakes up in bed with Rose on the day after her birthday party.
Charlie convinces Jake to take ballet as a way to romance the ballet instructor.
Alan begins a friendship with Charlie's senior citizen neighbor, only to discover how aggressive she can be.
Alan's obsession with getting women's approval leads to depression, so Charlie steps in to help.
Alan's latest girlfriend turns out to be a great cook and starts fattening up the boys, all the while establishing a nest in their home and slowly taking over the house.
Alan fears that Jake doesn't want to spend time with him, so Charlie sees his therapist for advice to help him.
Charlie is serious about his relationship with Mia, even though they haven't had sex yet, but no one believes him.
Mia discovers that Charlie hasn't told his former girlfriends that he is now dating her. Alan takes advantage and starts dating Charlie's previous girlfriend Kandi.
Charlie's latest girlfriend is trying to get him to live healthier, but Charlie schemes a way around it.
Alan is afraid to tell his mom that he is dating such a young woman.
Charlie is reluctant to attend the latest awards banquet for jingle writers since he has lost the last few years to the obnoxious Archie.
Alan's infatuation with Kandi starts to drain his bank account.
Charlie discovers that Kandi has been living with Alan and is not happy, until she makes friends with Judith.
Kandi leaves Alan to live with Judith, to Alan's dismay. Charlie hooks up with Kandi's mother while Kandi sets Judith up with her father.
Jake is forced to take place in a musical by his parents when they are told by his teacher that he has no outside interests
Jake is invited to his first boy-girl dance and he takes Charlie's advice, not his dad's.
Mia returns to town and Charlie tries to make everyone believe he is over her.
Charlie and Mia decide to marry, but when things start going bad, they decide to elope.
Alan wins a jackpot in Vegas after marrying Kandi, but soon discovers she does not love him and moves back in with Charlie.
Alan discovers that Mia wanted he and Jake to move out after she married Charlie; Charlie fights with his neighbor.
Charlie's attempt to woo a beautiful young girl by surfing go awry. 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's breakup with Kandi has cost him his condo and his car, but he draws the line at his dog. In an attempt to hold onto him, he hires the best lawyer for the job, the one Judith used against him.
When Alan learns that Herb is getting cold feet about marrying Judith, he pulls out the stops to get the lovebirds back together so he will be free from alimony.
Charlie dates a woman whose personality is unbelievably similar to his mother's, and everyone sees it except Charlie.
Charlie inadvertently agrees to help Berta confront the man who supposedly got her daughter pregnant. Alan reveals a preference for a certain type of woman.
Alan battles insomnia using therapy instead of medication.
Alan's failure to ever pick up the check at dinner has Charlie at his wits end, especially after learning of his load of money he has stashed away.
Charlie's girlfriend is pushy and arrogant and Berta decides not to take it. Alan tries to get Kandi's agreement to sell their condo but cannot convince her due to unexpected benefits.
Charlie's Christmas Eve plans with a beautiful girl go awry.
Alan secretly dates Berta's daughter, but Charlie finds out and worries about Berta's reaction.
Alan tells Judith and Herb that Jake can hear them having sex. The subject brings back unpleasant memories for Charlie.
Charlie's new neighbor seems uncannily like Alan, which prompts Charlie to try and fix them up with the hope that they'll fall in love---and he'll get rid of Alan.
Rose reveals her plans to move to London; Alan tries online dating.
Charlie is burning the rope at both ends to prove he is not old.
The death of Evelyn's friend leads to a discussion of how people feel about her, and she decides to make some changes.
When Alan realizes that Jake will be grown in no time, he tries to bond with his son. Meanwhile, Kandi decides to become an actress.
When Herb's sister arrives in preparation for his marriage to Judith, she attracts Charlie's advances.
Alan gets Jake ready for Judith's wedding. Meanwhile, Charlie continues to have a fling with Herb's sister.
Alan becomes friends with Greg, a single gay dad, which leads both Alan and Charlie to examine their own sexuality. Meanwhile, Jake develops a crush on Greg's daughter, Sophie.
Charlie takes Jake to the track, and a chance bet lands Jake a windfall. Meanwhile, Alan is stuck at the DMV.
Charlie loses his latest girl to his young, handsome handyman, which causes Charlie to set out to prove he is not getting old.
Their mother's new boyfriend invites Charlie and Alan to Las Vegas for the weekend, where each must deal with the prospect on a potential new father.
Charlie and Alan try to get Jake ready for his first day of junior high, but end up doing more harm than good.
Both Charlie and Alan have odd reactions to their respective nights -- Charlie spends an evening with his mother and Alan is given a weird response after having sex with his date.
After going out with too many bimbos, Charlie lets Alan set him up with a woman his own age.
Charlie nearly consummates his relationship with Linda, but when he sees Rose's face everywhere, he's unable to.
Alan discovers that Charlie hasn't had a paid gig for months and finds way to cut back on the expenses and earn a bit of extra cash. Charlie meets Linda's son and ends up spending a day with him.
Charlie is annoyed when his girlfriend is embarassed to be around him in public. Meanwhile, Jake sneaks out to go to a concert despite Alan forbidding him to do so.
Charlie and Alan fight over Alan's place in the household, leading Alan and Jake to move in to Evelyn's.
Charlie discovers he may have a new career as a children's singing star.
Teddy's daughter proves to be an irresistible temptation for Charlie.
Alan sets out to get Charlie back when he learns that Charlie stole his high school girlfriend from him.
Charlie teaches Alan the finer points on breaking up with a female.
A sick Charlie receives unique nursing from Rose, as she returns from England.
Alan goes on a date with an old friend of Judith's, who spends the night gossiping about Judith's past sex life.
As Charlie and Jake set up a double date, Charlie arranges for Alan to accompany a prostitute on his date.
Alan fears that Charlie's womanizing has gone too far.
Alan works to plan Evelyn's wedding. Meanwhile, Charlie has a fling with his future step-sister.
Evelyn and Teddy tie the knot but a shocking event requires the services of local police detectives.
Charlie finds himself drawn to an older author of self help books, while Alan and Jake are fighting over a assignment for school.
Charlie's current flame has an adult son who is engaged to a girl he used to date.
Charlie runs into a former girlfriend who's son looks a lot like he does.
After borrowing money from Alan, Charlie loses his temper when Alan demands repayment and kicks Alan out of the house.
Charlie decides to take a break from womanizing and experiments in the kitchen while Alan tries to juggle going out with two women.
Charlie works his magic on Alan's receptionist as Alan anticipates the worst.
The guys bump into Jake's former teacher who became a stripper after a fling with Charlie. Charlie tries to help her out by giving her a room and a job, but things spiral out of control.
When Herb gets kicked out of the house, Alan tries to resume his place with Judith.
Charlie tries to introduce Herb to his lifestyle while Alan works to free himself from Judith.
Charlie's latest girl is tired of always staying with him, and asks him to stay with her once and a while. Alan tries to enforce his parental authority.
When Charlie's intimidating new neighbor comes looking for Jake and his teenage daughter, Charlie tries to cover for him.
When Jake's grandmother offers to finance his higher education, Alan ponders the need to keep working.
Charlie re-examines his lifestyle when an old friend who led a similar life passes away.
Jake challenges Charlie in a play for the attention of an attractive waitress. Meanwhile, Alan and Melissa confront the attraction between them.
Judith is pregnant and Alan, after their one-night stand, worries that he might be the father. Meanwhile, Jake is in a bad mood and Charlie is convinced he knows why.
Alan begins to believe that his family doesn't appreciate him, leading him to move in with Melissa and her mother.
Charlie agrees to attend couples counseling with Chelsea.
Charlie panics when he has to remove a half-naked woman from his bedroom before Chelsea arrives.
Charlie admits to Chelsea that he is in love with her, but the response he receives is not what he had expected.
When Chelsea gets sick and Charlie has to take car of her, he must fight the urge to leave.
After Chelsea discovers a nude picture of another woman on Charlie's cell phone, he blows off steam by going out for a night of drinking with Alan, Herb and his neighbor.
Evelyn and Chelsea meet for the first time, and Charlie wants to make sure they never become friends.
Chelsea is asked by Alan to arrange a blind date between he and her new friend, unaware that her new friend is Rose.
Charlie mourns the loss of his bachelor pad as he reluctantly allows Chelsea to move in. Meanwhile, Alan discovers there is no longer much space left in the house for him.
As Alan and Chelsea bond, Charlie uses the free time to do the things that he likes to do on his own.
After hearing Mia is back in town, Charlie begins questioning his relationship with Chelsea. Meanwhile, Charlie, Alan and Herb rush Judith to the hospital when she goes into labor.
When Mia returns, Charlie must make a decision whether to return to her or stay with Chelsea.
After Chelsea strong-arms Charlie into letting Melissa move in with Alan, the girls end up taking over the house.
When Judith and Herb take a weekend away, they leave Judith's mother-in-law in charge of the baby, but Alan soon ends up caring for them both.
Alan goes to work for his mom to make extra money while Charlie tries to mend fences between Chelsea and Jake.
Jake stops at nothing to get away from Charlie and Alan, after they embarrass him out in public.
Charlie kicks Alan out after he suggests that Chelsea get breast reduction surgery.
Alan and Charlie both wake up next to a strange woman, leading them to try to figure out what had happened the night before.
Chelsea invites her college roommate to stay at the house after she has a bad break up.
Alan searches for a way to cure his baldness, while Charlie worries that he can't satisfy Chelsea.
Chelsea wants Charlie to take dancing lessons for the wedding, while Charlie uncovers the truth that Chelsea has been lying about her finances.
Charlie gives Jake a lesson in the art of infidelity when Jake's girlfriend goes away for Christmas.
In order to try to get his ex-girlfriend back, Jake decides to write her a love song. Meanwhile, Herb and Alan try to hide their secret friendship from Judith.
Charlie opts to have a colonoscopy in order to avoid going on a trip with Chelsea to see her parents. However, when he returns home, he finds her parents at his house.
Alan finds himself in jail after a bar fight, and Charlie worries that Chelsea might be attracted to the lawyer who takes the case.
Chelsea and Charlie's relationship is at risk when Charlie's jealousy comes between them.
Charlie mourns his breakup with Chelsea by running off to Vegas and returning with a new wife.
Charlie and Chelsea are both miserable after the breakup. They end up spending the night together, but nothing changes.
Charlie runs into Chelsea's best friend Gail again, while Alan new female patient pays him well for services rendered.
Jake gets a new friend, who Alan feels is a bad influence until he meets his attractive mother.
Alan takes Lyndsey to a hotel; Charlie tries something different as a replacement for Chelsea.
Alan and Jake take a trip together; Charlie is haunted by memories of previous girlfriends.
Charlie gets his license suspended so Jake becomes his driver; Alan plans to attend Chelsea's birthday party.
Alan has been hiding the fact that he is dating Jake's best friend's mother, and when Jake finds out he decides to move back in with his mom.
Lindsey asks Alan to move in with her and Charlie is beside himself convinving Alan to say "yes".
Alan makes the jump and moves in with Lyndsey, but secretly sees Melissa on the side at Charlie's house.
Alan, Lyndsey and her son move back in with Charlie after the fire Alan accidentally caused destroys Lyndsey's house.
Alan paints the town red while masquerading as Charlie sneaks off for some cosmetic surgery.
Charlie dates a slightly older woman, something that he is not used to and causes him some problems adjusting.
Charlie's girlfriend decides that she cannot handle his stalker, Rose.
Charlie and Alan try to set their mom up with Russell, their local pharmacist.
Berta's temporary replacement does such a good job that Charlie is enamored with her; Alan thinks Lyndsey's ex-husband is following him.
Charlie's old girlfriend Courtney shows up after three years in prison, and Charlie starts spending lots of money on her.
Alan's money woes causes him to look elsewhere for money to get a nice birthday gift for Lyndsey.
Charlie and Courtney break up, sending Charlie back to see his psychiatrist.
Charlie and Lyndsey's friendship grows and Alan becomes suspicious.
Charlie's becomes obsessed with the newly "married" Rose; Jake and Eldridge engage in stupid and dangerous stunts and film them in an attempt to make money.
Charlie and Rose continue their romantic liaisons; Alan's attempts to borrow money to expand his chiropractic business takes a surprising turn.
Charlie is tired of the short periods of time he can be with Rose and tries to convince her to go away with him; Alan battles with his conscience over scamming his family and friends in a Ponzi scheme and finds a way out from an unexpected source.
Charlie Harper's funeral attracts all of the women in his life that he wronged. Alan is in a pickle since Charlie's house must be sold. Alan meets a rich new friend that has more in common with Charlie than Alan originally thought.
Walden moves into Charlie's Malibu home as the new owner and Alan leaves, moving in temporarily with his mother. Walden is determined to get back with his wife and he takes Alan along for help.
Alan "temporarily" moves in with Walden. Walden solicits Alan's advice about women and also inadvertently gives Jake bad life advice.
Walden attempts to re-enter the dating game while Alan tries to reconcile with Lyndsey.
When Alan catches a late night movie featuring a nude Lyndsey, he confronts her about secrets and stupidly reveals secrets from his own past. Walden feels sorry for him and throws him a party with lots of girls in bikinis.
Walden's pending divorce becomes real when the divorce papers arrive from his wife. He must decide whether to run away from his problems or seek help. In the interim, he decides to get drunk and chases after a woman who reminds him of Bridget.
Walden wants to redecorate and Evelyn offers her professional services, among other things. Jake tries to make time with his tutor, who obsesses over Walden. Alan can't stop reading the journal that Charlie left behind.
When Walden sells Charlie's piano, Alan goes off the deep end and starts channeling his inner Charlie.
Alan returns from the nuthouse to find his life has descended into chaos.
Walden dates a British woman he met at the supermarket but struggles with his post-divorce feelings.
Walden has finally moved on from Bridget and is pulling out all the stops to impress his new girlfriend Zoey, when Bridget decides she wants to come back.
Walden is looking forward to spending Christmas with his mother and meeting Zoey's parents. However, his mother's visit triggers memories of his early childhood and his reaction is less than merry.
Walden is shocked when his mother and ex-wife team up to take over his company, for his own good. Walden seeks advice from Zoey and decides to ask Alan for help, but Bridget and Robin see Alan as a weak link and go after him.
Zoey asks Walden to clean up his act regarding his hair and beard in order to make him more presentable to her colleagues. Alan looks to get back with Lyndsey.
Zoey proves reluctant to discuss her and Walden's love life, so he tries some of Berta's special brownies as an icebreaker.
A storm that strands the two couples inside leads to fussin' and feudin' between Lyndsey and Zoey on Valentine's Day.
A perceived crisis causes Walden to utter the "L" word, and he is distraught when Zoey does not reciprocate. Lyndsey's drinking causes Alan some concern.
Walden and his former business partner make a temporary peace to work on a new project.
Alan and Lyndsey's plan to avoid spending time with their respective mother's backfires. Walden offers Jake and Eldridge advice regarding a high school party.
Walden is between a rock and a hard place when he tries to convince Zoey that his new business venture with his ex-wife is just business. Alan and Lyndsey try to make sense of the sudden friendship between their mothers.
Walden asks Zoey and Ava to move in with him and discovers a whole new set of challenges. Alan moves back in with Lyndsey and also encounters new challenges, challenges that might literally kill him.
Alan's injuries from the previous episode catches up to him and he ends up in the hospital after a minor heart attack. While there, he receives a surprise visitor that gives him life advice. Walden's panic over living with Zoey and Ava as a family takes a turn that surprises him.
After returning from the hospital, Alan is surprised by the outpouring of love being showered upon him by friends and family. Zoey, however, has her suspicions.
Jake graduates, and must decide what to do with his life. His decision surprises everyone.