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24 Episodes 2008 - 2009
Episode 1
Mon, Sep 22, 200822 mins
Charlie runs into ex-girlfriend Chrissy, whose son named Chuck looks, dresses, and acts disturbingly like Charlie, aged about a year younger then the affair he ended by humping her best friend. Alan takes great pleasure making fun of the situation. Charlie learns from his pharmacist that condoms are only 98% effective and, assuming Chuck is his son, pays Chrissy a large lump sum and promises her a monthly check for Chuck's maintenance. Just after Charlie leaves Chrissy's apartment, it is revealed that she is Chuck's babysitter, his name is actually Jeremy, and her plan to extort money from Charlie succeeded.

Episode 2
Mon, Sep 29, 200822 mins
Charlie kicks Alan out of the house again after Alan demands that Charlie pay him back the $38 he owes him. Alan and Jake are now forced to turn to Judith and Herb for a temporary home.
Episode 3
Mon, Oct 6, 200821 mins
Charlie seeks to broaden his horizons and improve his sex life by taking up basic cooking, but his focus on egg recipes has an unexpected result; meanwhile, he expresses concern when Alan and Jake try to emulate his lifestyle. Alan is dating two women at once, but lacks the liar talent or repertoire. Denied beer by his uncle, Jake gets drunk on a fake study date, but must be picked up; he's sick and vomits violently in Charlie's car. Because Alan is unable to lie convincingly, one of his dates finds out about the other--on whom he tries the "honesty is the best policy" but ends up tasered when he bothers her while she's with another partner.

Episode 4
Mon, Oct 13, 200821 mins
Alan is angry when Charlie hooks up with his secretary because he knows that the situation will end badly for him after their inevitable breakup.
Episode 5
Mon, Oct 20, 200822 mins
The boys bump into Jake's former teacher, Dolores Pasternak, who claims the way Charlie dumped her caused her to have a nervous breakdown, lose her job as a teacher and become a pole-dancer in a bikini bar. Atypically guilt-stricken, Charlie offers her a room at his house... well, Alan's room, banning the six year parasite to the couch... and offers her a job tutoring her ex-student Jake. But even her sexy way of making lessons interesting only works for short periods and even Charlie can't get the dumbo to understand about treating people well. When Charlie finds out she turned strictly religious, his solution is the same as the first time.
Episode 6
Mon, Nov 3, 200822 mins
Alan is overjoyed when he learns that Judith and Herb's marriage is on the rocks, but he gets more than he bargained for when he tries to fake-comfort her. Meanwhile, Herb tries picking up women with Charlie's help.
Episode 7
Mon, Nov 10, 200822 mins
Charlie warns Alan that recently divorced Judith lusting for sex with him is too good to be true, urging him to enjoy it while it lasts, but Alan gets romantic delusions again. The brothers are delighted to discover the threat of military school finally turns slacker Jake into drill master Charlie's obedient domestic slave. As Herb still turns to Charlie for dating expertise, Charlie soon learns Herb's marriage with Judith is up for repair, but gets drunk rather then warning Alan, who is thrown out again.
Episode 8
Mon, Nov 17, 200822 mins
Charlie's month-long relationship threatens to go down the tubes when Chelsea asks him to spend the night at her house instead. Alan grounds Jake for mooning some girls on a school bus.
Episode 9
Mon, Nov 24, 200822 mins
Alan realizes what a babe magnet Charlie's car can be while Charlie is left with the neighbor when his daughter disappears with Jake.

Episode 10
Mon, Dec 8, 200821 mins
When Evelyn offers to pay for Jake's college education and a car, Charlie suspects that she has an angle to play.
Episode 11
Mon, Dec 15, 200822 mins
Charlie contemplates making some changes in his life after an old buddy and partner in crime drops dead on the balcony of his beach house.

Episode 12
Mon, Jan 12, 200921 mins
Alan considers hooking up with his receptionist--until he meets her mother, and Charlie and Jake fight for the affection of a beautiful woman

Episode 13
Mon, Jan 19, 200922 mins
Judith is pregnant, Alan believes he is the father, and Judith tries to keep him away from Herb. Meanwhile, Charlie tries to figure out why Jake is so irritable.

Episode 14
Mon, Feb 2, 200930 mins
Dumped by Charlie earlier, Alan's receptionist Melissa is now her boss's lover. She forces Evelyn to co-host a 'surprise' birthday party for Alan in a restaurant's private room. Everybody is invited to sing his praise, but Jake hides in the loo while the other kin and Bertha rather insult Alan. Melissa, who brought her lunatic junkie mother Shelly, leaves indignant and insists Alan moves in with them. INitially spoiled by both, Alan is seduced by ma's banana space cake into her bed, so kicked out and crawl back to Charlie, who is surprised to have missed him a bit, Jake didn't even notice.
Episode 15
Mon, Feb 9, 200922 mins
Just when Charlie is happy practicing monogamy with Chelsea, she gets sick and he has to nurse her, then catches her bug and the roles are reversed. Despite getting through all that, she whines about the boring routine. Although Alan cynically warns Charlie that couples therapy spells disaster, Charlie consults Dr. Linda Freeman and even agrees to bring Chelsea for couples counseling. Out of frustration, Charlie gets addicted to comfort food, even confiscating Jake's marked desserts and painfully 'rewards' gloating Alan.
Episode 16
Mon, Mar 2, 200921 mins
Charlie objects to Alan calling him a sleazebag for getting yet another blonde nymphomaniac into his bed while Chelsea--for whom he admits having actual feelings--is at her ex-mother-in-law's funeral. When Chelsea phones to say she is on her way home early, Charlie commandeers Alan and Jake to help him remove the unconscious Wanda from the house. Jake seems to recognize Wanda but doesn't figure out that she's the girl on one of his pinup posters. Wanda wakes up most impractically.

Episode 17
Mon, Mar 9, 200921 mins
Charlie is so desperate to get Chelsea to return his accidental "I love you" and not lose control in the relationship that he is willing to propose to her just to make her say it.
Episode 18
Mon, Mar 16, 200922 mins
Just when Charlie is happy practicing monogamy with Chelsea, she gets sick and he has to nurse her, which he finds disgusting. Alan gloats that now the golden boy tastes the "joys of marital life", Berta sides with her and is atypically helpful, and pharmacist Russell recommends strong, even illegal stuff. When she's finally better, he catches her bug and the roles are reversed, again without sex, but he has nightmares of her cat Sir Lancelot, whom he and Alan had to tend in her absence.
Episode 19
Mon, Mar 30, 200921 mins
Charlie, Alan and Herb get together when they all have problems with their significant others: Charlie with Chelsea because of some topless photos an ex sent him, Alan with Melissa for sleeping with her mother while stoned and Herb with Judith because of arguments set off by hormones.
Episode 20
Mon, Apr 13, 200922 mins
Charlie is disturbed when his mother meets Chelsea and starts spending time with her, but he has a plan for revenge.
Episode 21
Mon, Apr 27, 200922 mins
Chelsea sets up Alan with her new "friend" Rose--the same Rose who stalked Charlie for years. But to Charlie's surprise, the two of them hit it off.
Episode 22
Mon, May 4, 200921 mins
When Chelsea's lease is up, Charlie reluctantly agrees that they should live together, but he has second thoughts about everything once the moving in process begins and Chelsea starts to nest, while the rest of the household has mixed reactions.
Episode 23
Mon, May 11, 200921 mins
Charlie is angry when Alan and Chelsea become good friends, until he figures out how to use the situation to his advantage.

Episode 24
Mon, May 18, 200922 mins
Chelsea is jealous when Charlie's ex fiancée, Mia, calls him--perhaps rightfully so. Meanwhile, Judith goes into labor, Herb is incapacitated, and Alan runs into his ex-girlfriend and receptionist at the hospital.