Alan and Walden have a meeting with an adoption social worker (guest star MAGGIE LAWSON) that hinges on them being convincing as a loving couple. Scrambling to make the beach house presentable, their plans are put in jeopardy when Lyndsey (recurring guest star COURTNEY-THORNE-SMITH) returns after 60 days in rehab.
Alan and Walden befriend three moms at a kids’ gym, but things get complicated when Walden becomes attracted to one of them. Meanwhile, Alan’s invited along for a wild girls’ night out with a group of moms.
On the eleventh season premiere, Alan and Berta (series star CONCHATA FERRELL) are shocked when Charlie's long-lost illegitimate daughter (Tamblyn) shows up at Walden's beach house to connect with what's left of her family. Having moved to LA to pursue acting, 25-year-old Jenny likes everything her dad liked...including women.
When Walden feels cramped in his own house, Jenny moves in with Evelyn (recurring star HOLLAND TAYLOR) and her wealthy boyfriend, Marty (recurring guest star CARL REINER). Meanwhile, Alan becomes Lyndsey's "other man."
Alan befriends Lyndsey's boyfriend Larry (guest star D.B. SWEENEY) in an effort to find out what he has that Alan doesn't. Meanwhile, Walden helps Jenny be more proactive in pursuing her acting career.
When Alan learns Walden knows Wonder Woman's LYNDA CARTER (guest starring as Herself), he asks him to set him up on a date with her. Against his better judgment, Walden agrees to invite her to the house for dinner. MIMI ROGERS returns as Walden's mother, Robin.
When Larry hires a private investigator to follow Lyndsey, he tracks her to the beach house. But when Larry thinks that she's having an affair with Walden, Alan has to figure out how to clear Walden's name without outing himself. Recurring guest star MELANIE LYNSKEY returns as the neighborhood stalker Rose, who offers to help Walden out of his dilemma.
Walden's date with a gorgeous, accident-prone underwear model (guest star KATE MINER) goes on much longer than he expected. Meanwhile, Alan dates a woman who shares some surprising personal information with him.
Walden helps Jenny get a second date with a one-night stand (guest star ALY MICHALKA) and Alan's transgender girlfriend's ex-wife (guest star DIANE FARR) hits on him. Meanwhile, in the spirit of the holidays, Alan receives a Japanese delicacy from Jake for Christmas, and Walden's Malibu house is alive with questionable Christmas carol lyrics. Paula Marshall returns as Alan's transgender girlfriend, Paula.
Walden joins his beautiful former employee, Nicole (guest star ODETTE ANABLE) on a brilliant new project. Meanwhile, Alan advises Jenny to open up to her girlfriend Brooke (guest star ALY MICHALKA) or risk losing her.
After multimillionaire Marty Pepper proposes to Evelyn, Walden and Alan throw him a bachelor party with several of his old friends (comedy legends TIM CONWAY, STEVE LAWRENCE and GARRY MARSHALL guest star) who help him celebrate his last days of bachelorhood.
Walden gets an invitation to his ex-girlfriend's boutique opening. Meanwhile, Gretchen wants to spend more time at Alan's (aka Jeff Strongman) house. BROOKE D'ORSAY returns as Walden's ex-girlfriend Kate.
Walden reconnects with Kate and is sure she's "The One" -- that is, until he meets Vivian (guest star MILA KUNIS -- That '70s Show, Black Swan), a beautiful, free-spirited world traveler who shows up on his doorstep. Feeling an instant connection with Vivian, he soon becomes convinced that she's "The One." Meanwhile, Alan and Gretchen grow closer.
Alan confesses his true identity to Larry and has to face the consequences on the Season Eleven Finale. Guest star Kimberly Williams-Paisley returns as Alan's fiancée Gretchen, alongside her real-life husband BRAD PAISLEY who makes a cameo appearance.
On the tenth season premiere, Walden plans a big surprise for Zoey (recurring guest star SOPHIE WINKLEMAN) on her birthday. Grammy winner MICHAEL BOLTON guest stars as himself, while True Blood's BRIT MORGAN guest stars as a woman Walden meets at a bar.
Walden starts to feel his age when a friend's daughter comes to town. Actress MILEY CYRUS guest stars as Missi, the friend who comes to visit for a week and develops a relationship with Jake when he comes home from the Army.
Walden asks Rose to move in, but she feels that it's too early in their relationship. When Zoey tells Walden that she wants to get back together, however, he has to choose between Rose and Zoey...before it's too late.
Tired of the complications of a traditional relationship, Walden hires an actress (guest star LINDSAY PRICE) to play the part of his girlfriend. But when he starts falling for her, he can't tell if she really has feelings for him or is just acting. Meanwhile, Jake and Missi (MILEY CYRUS) surprise Walden and Alan when they plan a weekend rendezvous at the beach house. Too bad, the Army is looking for him as well.
Alan is hesitant to make a serious commitment to Lyndsey (recurring guest star COURTNEY THORNE-SMITH), but gets inspiration from an unlikely source. Meanwhile, Walden enjoys being a boy-toy for a rich older woman.
Alan and Lyndsey's relationship is strained when he won't give her a key to the beach house. Meanwhile, Walden, Billy and Herb (recurring guest star RYAN STILES) commiserate about women and relationships. WILLIE GARSON guest stars as Dr. Steven Staven, Lyndsey's gynecologist who takes her on a date.
Alan moves out after he and Walden get into a fight over a broken toaster. After Alan moves in with Herb, Walden feels bad and tries to apologize. But Herb gets in the way... because he doesn't want to lose his new roommate.
When Jake cheats on his girlfriend Tammy (JAMIE PRESSLY) with her 18-year-old daughter, Ashley (guest star EMILY OSMENT) Alan and Walden get caught in the crossfire. SCOTT BAKULA guest stars as Ashley's ex-boyfriend Jerry.
Even though Walden's dating a hot 22-year-old woman (guest star HILARY DUFF), he finds himself more attracted to her worldly grandmother, Linda (guest star MARILU HENNER). Meanwhile, Alan and Jake go on a father-son bonding trip on the tenth season finale.
Trying to rebound from his recent separation, Walden goes looking for Mrs. Right, while Alan has an opportunity to reconcile with his on-again, off-again girlfriend Lyndsey (guest star COURTNEY THORNE-SMITH).
Walden receives divorce papers from Bridget, but forgets his depression when he meets a girl who looks eerily like her. JOE MANGANIELLO (True Blood) guest stars as Bridget's new beau, Alex and JANE LYNCH (Glee) returns as therapist, Dr. Freeman.
Things get tense in the Malibu house when Walden's estranged ex-business partner, Billy (guest star PATTON OSWALT), shows up looking to bury the hatchet with a money-making idea. Will their combustible relationship get in the way of their success? Meanwhile, a lonely Alan pays a visit to Berta.
Alan and Lyndsey introduce their mothers (HOLLAND TAYLOR and GEORGIA ENGEL) to one another, so that they can have more time together. Meanwhile, Jake and Eldridge enlist Walden to drive them to a high school house party that they never find.
On the eighth season premiere, Jake (series star ANGUS T. JONES) finds out that Alan (series star JON CRYER) has been dating Eldridge's mom (recurring guest star COURTNEY THORNE-SMITH), so he packs up and heads to Judith (series star MARIN HINKLE) and Herb's (recurring guest star RYAN STILES). Meanwhile, Charlie (series star CHARLIE SHEEN) decides it's time to cut back on boozing.
When Berta takes a couple of days off, Charlie falls for her replacement (guest star TONITA CASTRO). Meanwhile, Alan believes he's being stalked by Lyndsey's ex-husband. Courtney Thorne-Smith returns as Alan's former girlfriend, Lyndsey and Judd Nelson returns as her ex-husband.
Charlie goes on a spending spree for his old fling, Courtney (guest star JENNY McCARTHY), who shows up after three years in prison for conning him out of money. Guest star CARL REINER returns as Marty, Evelyn's old fling.
On the seventh season premiere, Charlie (series star CHARLIE SHEEN) must decide between his fiancée, Chelsea (recurring guest star JENNIFER TAYLOR), and his old flame, Mia (recurring guest star EMMANUELLE VAUGIER). Rock superstar EDDIE VAN HALEN makes a cameo appearance as himself.
Alan (series star JON CRYER) plays nursemaid to Judith's baby and her tipsy mother, Lenore (recurring guest star ANNIE POTTS). Meanwhile, Jake (series star ANGUS T. JONES) blackmails Charlie with an incriminating photo.
Charlie coaches Jake on the art of infidelity while his girlfriend is away for Christmas. Legendary Television Producer/Writer/Actor CARL REINER guest stars as "Marty Pepper," a famous TV producer whom Evelyn invites to Charlie's for Christmas dinner.
Charlie has a return engagement with Chelsea's best friend, while Alan has an unexpected effect on a new female patient. TRICIA HELFER returns as Chelsea's best friend and FRANCES FISHER guest stars as Alan's patient.
Alan and Jake go on a road trip while Charlie is visited by the ghosts of girlfriends past -- including guest stars KATHERINE LANASA, MING NA, EMMANUELLE VAUGIER, RACHEL CANNON, AJA EVANS, MAGDALENA HOLLAND, REBECCA MCFARLAND, KATY MIXON, JODI LYN O'KEEFE, MISSI PYLE AND RENA SOFER. ZZ TOP also makes a special appearance as themselves, while MARTIN MULL returns as Charlie's pharmacist Russell.
After Charlie's license is suspended, Jake becomes Charlie's driver. And much to Charlie's chagrin, Alan makes plans to attend Chelsea's birthday party on the seventh season finale. STACY KEACH and JOHN AMOS return as Chelsea's father and his boyfriend.
The guys bump into Jake's former teacher, Miss Paternak (guest star ALICIA WITT) 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.
One of Charlies old partners in crime dies, leaving Charlie to reevaluate his own reckless lifestyle. Charlie Sheens brother EMILIO ESTEVEZ guest stars as Charlies old friend Andy, along with Oscar® nominee JAMES EARL JONES as himself.
Charlie and Jake fight for the affections of a waitress (guest star EMILY ROSE), while Alan fights sexual tension with his receptionist, Melissa (guest star KELLY STABLES). Multiple Emmy® Award winner CAROL KANE ("Taxi") guest stars as Melissas mother.
On the sixth season finale, Charlie starts to question his relationship with Chelsea when he hears that Mia (guest star EMMANUELLE VAUGIER) is back in town. Meanwhile, Judith goes into labor and Charlie, Alan and Herb rush her to the hospital.
Tired of dating vapid young women, Charlie allows Alan to introduce him to a sophisticated, intelligent municipal court judge, Linda (recurring guest star MING WEN - "ER," "The Joy Luck Club"). Unfortunately, intimidated Charlie behaves so badly at dinner that Linda refuses to see him again -- until he ends up in her court. Meanwhile, Jake won't stop talking on his cell phone.
In the landmark 100th episode, Charlie gets closer to consummating his relationship with Linda (recurring guest star MING WEN), but he keeps seeing Rose's (former series star MELANIE LYNSKEY) face everywhere he turns. Recurring guest star JANE LYNCH appears as Dr. Freeman.
After Evelyn and Teddy (recurring guest star ROBERT WAGNER - "Hart to Hart," "Austin Powers: The Spy Who Shagged Me") become engaged, Charlie struggles to fight his attraction to Teddy's daughter, Courtney (guest star JENNY McCARTHY - "Scary Movie 3," "Dirty Love"), Charlie's soon-to-be stepsister.
While trying to help Jake get over a breakup, Alan discovers that it was Charlie who stole his high school girlfriend. Alan seeks revenge on Charlie by following the same advice Charlie dispenses to Jake.
In the season premiere, Charlie deals with the immediate aftermath of his canceled wedding--and Alan's impulsive new marriage to 22-year-old Kandi (series star APRIL BOWLBY). Still in Las Vegas, Alan and his materialistic bride find out that Alan's lucky streak is not over when he wins $500,000 on one play of a slot machine. Four months later, Alan visits his brother's home to find that Charlie is taking full advantage of having the house all to himself. But Alan has some life-altering news to share: he's getting divorced.
Alan feels guilty when Charlie finally tells him why he broke up with Mia. The truth is that Charlie and Mia didn't get married because she had wanted Alan and Jake to move out. Meanwhile, problems arise when Charlie and his famous rock star neighbor, STEVEN TYLER (himself) of Aerosmith, don't get along.
Charlie attempts to surf in order to impress a beautiful girl--with disastrous results. Later, after nearly drowning, he tells Alan that when Charlie's life was hanging in the balance, the guys' deceased father appeared to him and made a request that Charlie is reluctant to fulfill.
Alan and Kandi become embroiled in an unconventional custody battle. Alan is determined to retain custody of his and Kandi's dog after Kandi walks away from their split with both the condominium and the car. Having also lost everything to Judith following their divorce, Alan decides to hire the best lawyer he knows--Judith's.
Alan is overjoyed that he'll no longer owe Judith alimony when she marries her new fiancé, Herb (recurring guest star RYAN STILES - "The Drew Carey Show"). However, when Judith and Herb's marriage plans are threatened due to Jake's disdain for his soon-to-be stepfather, Alan enlists Charlie's help, and the guys bond with Herb in an effort to improve his relationship with Jake.
Although Charlie doesn't get along with his sharp-tongued, passive- aggressive mother, he is strangely attracted to Lydia (recurring guest star KATHERINE LaNASA - "Justice"), a blonde high-end real estate agent--which is exactly what his mother is. Unfortunately, the similarities don't end there, and the relationship soon begins to seem a little too familiar for comfort.
When Berta swears vengeance on the married man who got her daughter, Naomi (recurring guest star SARA RUE), pregnant, she forces Charlie to come with her. Meanwhile, Naomi helps Berta with the housework. And Alan reveals an unusual fetish.
Unable to sleep, Alan takes Charlie's suggestion and goes for a jog on the beach. After his run takes a disastrous turn, Alan turns to a psychiatrist in the hope that discovering the source of his insomnia will help alleviate it. Meanwhile, Jake pleads with Charlie not to date the hot mother of a classmate whom Jake likes.
During a double date, Charlie becomes annoyed with Alan for constantly borrowing money and promising to pay the tab "next time." When Alan leaves Charlie with the check after dinner, Charlie tries to beat him at his own game. Meanwhile, while the men are out, Jake gets to see what it's like to be home alone.
Charlie must choose between his girlfriend Lydia (recurring guest star KATHERINE LaNASA) and Berta as they fight for his allegiance, each thinking the other has crossed the line. Meanwhile, Alan wants to sell an overpriced condominium that he and Kandi bought when they were married, but Kandi uses her assets to distract him.
As Charlie prepares for a steamy Christmas Eve alone with his date, his friends and family keep dropping in--and staying--until Charlie finds himself hosting an unplanned, unwanted holiday party. Upon discovering whom Charlie's new girlfriend is, Evelyn inexplicably becomes desperate to break them up before they go too far in their relationship. SUSAN SULLIVAN ("Dharma & Greg") guest stars as Dorothy, the mother of Charlie's date. Recurring guest star RYAN STILES appears as Judith's fiancée, Herb.
When Berta discovers that Alan has been secretly dating her daughter, Naomi (recurring guest star SARA RUE), Alan expects trouble. But Berta's reaction is surprising--and much worse--than Alan could have imagined.
Jake tells Charlie and Alan that he often overhears Judith and her fiancé, Herb (recurring guest star RYAN STILES), having sex, and he formulates a theory as to why his mom constantly gives Herb directions in bed. Meanwhile, Rose (recurring guest star MELANIE LYNSKEY) helps Charlie work through a disturbing repressed memory, triggered by Jake's revelation.
After getting to know Danielle (BROOKE SHIELDS - "Nip/Tuck," "Suddenly Susan"), the guys' hot new neighbor, Charlie discovers that she shares some common interests with Alan and proceeds--with ulterior motives--to set them up. But when things begin to heat up between Alan and Danielle, Charlie becomes jealous and attempts to sabotage the relationship.
When Rose announces that she is moving to London permanently, Charlie doesn't listen at first. But he eventually realizes that he must face his true feelings for her. Meanwhile, Alan tries online dating--with unforeseen results. After exaggerating while writing his profile on an internet dating service, Alan attracts a fellow profile embellisher, Beverly (ALLISON JANNEY - "The West Wing").
A sexy young girl whom Charlie has been dating cajoles him into going to a hot new club and bringing Alan along to meet her friend. But when they arrive, Charlie and Alan are mortified to learn that the partygoers consider them old. MORGAN FAIRCHILD ("Falcon Crest") guest stars as Donna, a more mature woman who helps rebuild Charlie's ego.
After Alan and Charlie tell Evelyn that none of her acquaintances will mourn her when she dies, she bitterly ignores them for a few weeks. The guys then discover that, instead of trying to be more pleasant to the people she knows, Evelyn has brought together a whole new group of "friends," including two men and a cute boy who seem suspiciously like adoring versions of Charlie, Alan and Jake. Meanwhile, Jake develops an interesting new way of speaking.
When Jake starts covering his walls with posters of sexy women, Alan realizes that his son is almost grown up. He makes a last-minute attempt at father-son bonding, wanting to make the most of what little childhood Jake has left. Meanwhile, Kandi embarks on a new career as an actress.
As Judith and Herb's (recurring guest star RYAN STILES) wedding nears, Charlie gets close to Herb's witty sister, Myra (recurring guest star JUDY GREER - "Arrested Development"). But Charlie's flirtation does not please Judith, who orders Alan to make Charlie stop pursuing Myra.
While Alan prepares Jake for Judith's wedding, Charlie continues his fling with Herb's (recurring guest star RYAN STILES) sister, Myra (recurring guest star JUDY GREER). Besides Judith's disapproval of the relationship, Charlie gets a surprise from Myra after admitting that he truly likes her.
When Greg (MATT ROTH), a single father from Alan's support group who has been spending a lot of time with Alan, reveals that he is gay, Charlie suspects that Greg is attracted to Alan. Alan initially refuses to believe that his friendship with Greg is anything romantic, but he soon questions his own sexuality--as does Charlie. Meanwhile, Jake is too clueless to realize that Greg's young daughter is flirting with him.
Jake experiences a windfall when Charlie takes him to the racetrack. Meanwhile, Alan is stuck in a hellish Department of Motor Vehicles office. Series star JON CRYER made his directorial debut with the episode. JOEL MURRAY ("Dharma & Greg") guest stars as Petey.
Charlie loses a woman he is dating to a young, handsome handyman, Fernando (Grammy Award-winning recording artist ENRIQUE IGLESIAS), who is working on Charlie's house. Meanwhile, to Alan's consternation--and no one's surprise--Jake finds out that he must attend summer school because of his poor grades.
Charlie and Alan must confront their "daddy issues" when Evelyn's new boyfriend, Teddy (ROBERT WAGNER - "Hart to Hart"), invites them to Las Vegas on his private jet. MIKE CONNORS ("Mannix") guest stars as Hugo.
After Alan falls off the roof trying to fix the satellite dish, Charlie volunteers to take care of Jake for the weekend. While Charlie initially looks forward to watching his nephew, he quickly realizes that Jake's idea of fun--going out for fast food and renting video games--doesn't quite coincide with his own. Alan finally convinces Charlie that the situation will be more peaceful if Charlie simply agrees to Jake's demands. A power struggle ensues, with Jake initially winning--until he sabotages a potential date for Charlie. Meanwhile, Evelyn insists on arranging a blind date for Alan.
When Jake's school principal demands to meet immediately with Alan concerning a picture Jake drew of a large-breasted schoolmate, Alan leaves a phone message asking Charlie to help, but Charlie doesn't respond. After Alan accuses him of "not being there for him," Charlie agrees to answer phones at Alan's chiropractic office, where Charlie proceeds to hire a "masseuse" to help out with the practice. Meanwhile, before the principal determines Jake's fate, she makes Alan meet the classmate's mother--whom Alan tries hard not to offend.
Charlie is dismayed to learn that Alan's recent dating spree has been with Alan's ex-wife, Judith. Charlie fears he will rarely get to see Jake if Alan and Judith reconcile. So Charlie does everything in his power--including trying to distract Alan with beautiful women (Former Playboy Playmates SANDY and MANDY BENTLEY)--to keep the two apart. As it turns out, Charlie underestimates his brother's ability to screw things up on his own.
Alan infuriates Charlie when he gives Berta permission to move into the beach house for a couple of days. Charlie reprimands Alan and informs him that he's just a houseguest and doesn't have the right to allow Berta to stay with them. Hurt by Charlie's reaction, Alan decides that he and Jake need to move into their own place. But after he returns from apartment hunting with their mother, Alan begs Charlie to let him and Jake remain. Neither man realizes that Berta goaded the brothers into the argument so she could permanently move in with Charlie.
After a woman Charlie has been having sex with professes her love for him, he responds inappropriately and suffers from impotence. Later, Rose explains that Charlie's inability to have a long-lasting relationship is due to unresolved issues with his mother. Meanwhile, much to Alan's chagrin, Jake approaches Charlie for relationship advice regarding a girl at school who likes him.
Charlie is thrilled that he's dating Isabella (JODI LYN O'KEEFE - "Nash Bridges"), a wild, sexually uninhibited woman--until Alan points out that she's a spooky Satan worshiper. Charlie is unfazed by Alan's warnings until Isabella threatens to put a curse on his manhood.
Charlie finds himself in a compromising position after getting drunk and spending the evening with his stalker, Rose, celebrating her birthday. He ends up being confronted by her father, Harvey (Golden Globe and Emmy Award winner MARTIN SHEEN - "The West Wing"), who demands to know Charlie's intentions towards Rose.
After Charlie's romantic overtures towards Mia (recurring guest star EMMANUEL VAUGIER - "Smallville," "One Tree Hill," "Saw II"), an attractive ballet teacher, are rejected, Charlie tries to prove to Alan that he can persuade Mia to go on a date with him. Charlie cons Jake into taking her ballet class so Charlie can get close to her, but his plan is derailed when Jake becomes infatuated with her.
Alan organizes a family dinner to celebrate the publication of a newspaper article that describes him as a "good doctor, good neighbor and a good guy," but he's crushed when his mother, Evelyn, isn't impressed. After getting drunk, Alan experiences a life-changing epiphany and vows to a skeptical Charlie that he is no longer going to grovel for validation from his mother and the other women in his life.
When Alan dates a cooking instructor, Sandy (JOSIE DAVIS - "Beverly Hills 90210"), both he and Charlie gain weight. But even as it becomes clear that Sandy is mentally unstable, Charlie refuses to allow Alan to break up with her, fearing the loss of her fabulous meals. Meanwhile, as usual, the brothers agonize over whether or not to visit their mother for Christmas.
Charlie and Alan take Jake to a friend's house and go out for some sibling bonding at the movies, but their night is ruined when Alan freaks out after convincing himself that Jake was too eager to spend the weekend away from him. Recognizing that desperate times call for desperate measures, Charlie begins seeing a psychiatrist, Dr. Linda Freeman (JANE LYNCH -- "The 40-Year-Old Virgin"), ostensibly to learn how to cope with his brother's ever-increasing emotional instability.
No one believes Charlie when he says that his relationship with Mia (recurring guest star EMMANUELLE VAUGIER) is getting serious, and everyone really thinks he's lying when he confesses that he and Mia have been dating for more than a month and haven't consummated the relationship. After a continuing series of chaste dates--walking on the beach, visiting an art gallery, going bowling--that end with Charlie frustrated at Mia's doorstep, he makes a proposal that threatens their burgeoning romance.
After a month and a half of abstinence, Charlie is quite eager to consummate his relationship with Mia (recurring guest star EMMANUELLE VAUGIER). Unfortunately, there are still a few roadblocks, including Charlie's oversexed ex-girlfriend, Kandi (recurring guest star APRIL BOWLBY), and Mia's parents. When the big day finally comes, Charlie worries that he may not be at the top of his game. Meanwhile, Alan discovers the joys of dating Kandi, although intellectually she may have more in common with Jake.
Charlie's lifestyle causes tension with Mia (recurring guest star EMMANUELLE VAUGIER). Charlie can't keep pace with the healthy routine that Mia has introduced into their relationship, so he sneaks cigars and beers in the garage and enlists Rose to deliver burgers to him on the sly. When Mia catches him lying, Charlie has to figure out if he is truly in love with her.
Concerned that he is dating a woman half his age--and mortified to introduce her to Evelyn--Alan tries to avoid bringing his sexy 22-year-old girlfriend, Kandi (recurring guest star APRIL BOWLBY), to Jake's birthday party. Meanwhile, Rose continues her passive-aggressive pursuit of Charlie.
When he is nominated for an advertising award, Charlie boycotts the banquet, having lost several years in a row to his cocky competitor, Archie (JON LOVITZ - "Saturday Night Live," "Happiness"). After devising a ploy to get him to attend, Alan, Evelyn and Jake accompany Charlie for support--but then they get to know Archie. Meanwhile, Rose talks Charlie into giving relationship advice to her new beau.
Alan gets into financial trouble because he keeps paying the expenses of his young girlfriend, Kandi (recurring guest star APRIL BOWLBY). When Kandi's old car breaks down, Alan leases a new one for her. Charlie warns him to break up with her, but Alan spends his last dime on Kandi's root canal and can't pay alimony to Judith, forcing Charlie to cover for him.
Kandi (recurring guest star APRIL BOWLBY) moves in with Alan and Charlie, causing tension in the house. Charlie's not happy to learn of the new arrangement, considering he himself has been having a dry spell with women. Things begin to look up for Charlie, however, when Judith befriends Kandi, and a special visitor comes knocking on his door. Recurring guest star Gail O'Grady (""Hot Properties,"" ""American Dreams,"" ""NYPD Blue"") appears as Kandi's mother, Mandi.
Charlie is now dating Kandi's (recurring guest star APRIL BOWLBY) mother, Mandi (recurring guest star GAIL O'GRADY). Meanwhile, Alan is depressed because Kandi has left him and is staying with bitter Judith, who brainwashed her against him. At Mandi's urging, Alan goes to Judith's place to try to win Kandi back. Also, Kandi introduces Judith to Kandi's father, Andy (KEVIN SORBO - "Hercules: The Legendary Journeys," "Andromeda").
Jake's teacher, Francine (JULIA CAMPBELL), calls Alan and Judith into her classroom to discuss Jake's lack of interest in school. Desperate to communicate with someone intelligent while continuing to see his airhead girlfriend, Kandi (recurring guest star APRIL BOWLBY), Alan falls for Francine--in a platonic way. Meanwhile, after Alan and Judith force Jake to try out for the school musical, Charlie helps him prepare.
When a cute girl from Jake's school invites Jake to a party, Charlie butts in on Alan's milestone moment with his son by offering his own words of wisdom on women. While Alan feels somewhat jealous that Charlie is taking over, he realizes he also feels envious that his son is receiving some solid advice on scoring with women that he wishes his brother had taught him.
When Charlie finds out that his ex-girlfriend, Mia (recurring guest star EMMANUELLE VAUGIER), is in town with her dance troupe and wants him to come to her performance, he opts not to go and tries to behave as if he were no longer attracted to her. After surprising Alan--and himself--by showing up at the dance performance, Charlie gets another surprise when Mia explains that she wants something personal from him: his sperm. Shockingly, commitment-phobic Charlie responds by asking Mia for something as well.
With Charlie and Mia (recurring guest star EMMANUELLE VAUGIER) arranging their wedding, their families meet, and things immediately begin to fall apart. Rose takes Charlie's engagement news hard and makes some interesting plans of her own. There is also the question of where Alan and Jake will live after Charlie and Mia get married. Ultimately, Charlie and his bride-to-be end up deciding on a small ceremony in Vegas--but the surprises don't end there.
Charlie Harper (series star CHARLIE SHEEN) is a well-to-do bachelor with a house at the beach, a Jaguar in the garage and an easy way with women. His casual Malibu lifestyle was interrupted when his tightly wound brother, Alan (series star JON CRYER), and Alan's young son, Jake (series star ANGUS T. JONES), came to stay with him. Complicating matters further are Charlie and Alan's narcissistic, emotionally toxic mother, Evelyn (series star HOLLAND TAYLOR--not appearing in this episode); Alan's deeply neurotic ex-wife, Judith (series star MARIN HINKLE); Charlie's domineering, unapologetically blue-collar housekeeper, Berta (series star CONCHATA FERRELL--not appearing in this episode); and Rose (series star MELANIE LYNSKEY), a brilliantly manipulative and vaguely crazy neighbor who had a brief fling with Charlie, remains obsessed with him and is determined to stay in his life by whatever means necessary.
At Charlie's urging, Alan decides to put his past behind him and returns a ceramic giraffe he vindictively took from Judith during the divorce. However, Judith does not remember the keepsake, and more importantly she has an attentive new boyfriend, Dr. Melnick (RYAN STILES - "The Drew Carey Show," "Whose Line Is It Anyway?"), who is Jake's pediatrician. Alan becomes even more depressed until Charlie reminds him that if Judith remarries, Alan won't have to pay alimony anymore. So, Alan awkwardly tries to encourage the relationship. Meanwhile, Evelyn questions an extremely uncomfortable Charlie as to why he hates her. Soon, Rose and Berta join the interrogation.
Jake thinks he's dreaming late one night when he sees the teacher who tried to get him suspended, Miss Pasternak (MISSI PYLE - "Bringing Down the House"), practically naked in Charlie's kitchen. When Jake refuses to go to school the next day, Charlie agrees to end the relationship with Miss Pasternak. Unfortunately, she gets upset, and Charlie and Jake both suffer.
Jake adores Judith's rich, new boyfriend because the man has a boat and a pool, and he promises to teach Jake how to snorkel and scuba dive. Feeling inadequate, Alan teaches his 11-year-old son how to drive a car. But when Judith's boyfriend ends the relationship, Jake becomes furious at his mother. Now it's Judith's turn to feel inadequate, and Alan does something he may regret.