Original air date: 09/27/2004 Runtime: 21:29 min. 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.
Original air date: 10/04/2004 Runtime: 20:08 min. 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.
Original air date: 10/11/2004 Runtime: 21:25 min. 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.
Original air date: 10/18/2004 Runtime: 21:22 min. Charlie dates a woman, Sherri (JERI RYAN - "Boston Public, " "Star Trek: Voyager"), who is a self-centered, manipulative narcissist--a female Charlie. But Charlie doesn't like the way Sherri treats him. Meanwhile, Alan tries to instill some discipline in Jake to improve his son's homework habits.
Original air date: 10/25/2004 Runtime: 21:29 min. When Evelyn tells Jake that Alan shoplifted a toy as a child, Alan denies the charge, as he has ever since the incident took place. He finally admits to Charlie his theory that maybe there is a "Bad Alan"--an evil side of him that stole the toy--which the good side of him works daily to suppress. Charlie feels guilty and admits to planting the toy on him, destroying the brother's relationship--until Evelyn offers to get involved.
Original air date: 11/08/2004 Runtime: 21:23 min. In order to serve as a good example to Jake, who has been disrespectful lately to his mother, Charlie and Alan begrudgingly agree to give their own mother a party to celebrate her real estate achievements. Berta suggests they hire her sister, Daisy (CAMRYN MANHEIM - "The Practice"), who owns a catering company. But having recently split from her husband, an emotionally unhinged Daisy throws a party that is unforgettable for all the wrong reasons.
Original air date: 11/15/2004 Runtime: 21:25 min. Alan's expectations for a first date with Nancy (KELLEY WEST), a woman he met while shopping for groceries, are far exceeded when she introduces him to a world of sex he never knew existed. Charlie is happy that his brother is getting to experience the kind of sex life he's always enjoyed, but he's not thrilled to take responsibility for Jake while Alan has his every fantasy fulfilled. When Alan starts thinking he loves this woman, Charlie realizes he must take action.
Original air date: 11/22/2004 Runtime: 21:59 min. Charlie encounters Lisa (recurring guest star DENISE RICHARDS, series star CHARLIE SHEEN's real-life wife), the woman he thought was "the one" until she informed him of her engagement to another man. He's thrilled to learn that her marriage did not work out, even though there's now a new wrinkle in their potential relationship--a baby (played by Sheen and Richards' daughter, SAM, in her first screen appearance).
Original air date: 11/29/2004 Runtime: 21:14 min. Charlie writes the theme song for a new cartoon based on one of Jake's favorite comics, but Jake hates the song. Realizing that Jake knows the comic better than he does, Charlie enlists his nephew's help. Meanwhile, Rose invites Alan to a movie and surprises him with her intellect.
Original air date: 12/13/2004 Runtime: 21:30 min. Charlie is surprised when a woman, Gail (JODI LYN O'KEEFE - "Nash Bridges"), with whom he flirts in a bar, rejects his overtures and tells him that women around town have been comparing notes on his philandering. Later, Jake mentions that he did an Internet search on Charlie's name and found something interesting. When Charlie logs on, he finds out that he's the subject of a very uncomplimentary new website called www.charlieharpersucks.com.
Original air date: 01/03/2005 Runtime: 21:28 min. Jamie (PAGET BREWSTER - "Huff, " "Friends"), Alan's close high school friend, visits Alan at the house. Charlie used to make fun of Jamie when they were teenagers, but when the two brothers see how attractive she is now, they both vie for her affections. However, Jamie has a plan of her own.
Original air date: 01/17/2005 Runtime: 20:48 min. When an earthquake causes plumbing damage in Judith's home, Alan allows her to move into the beach house temporarily--much to Charlie's displeasure. After a few days, Charlie and Jake can no longer bear Judith's presence, and though he pretends otherwise, Alan is jealous when Judith goes on a date with another man. He gets so upset that he goes to stay at Judith's house until Charlie arranges a date for Alan with a very beautiful and very young woman. Seeing Alan with this sexy girl, Judith quickly packs her belongings and returns to her own home. But unfortunately for Charlie, he's going to have to keep paying the young lady big money because Alan really likes her.
Original air date: 01/31/2005 Runtime: 21:29 min. After Evelyn undermines Jake's confidence by belittling his hard-earned high grade on a test, Alan decides to cut her out of their lives. When Charlie and Alan receive news that Evelyn is in the hospital, they realize it's a ploy for her to get back into their lives. They decide to play along, pretending to schedule her for heart surgery, but they don't realize that Evelyn is still one step ahead of them.
Original air date: 02/07/2005 Runtime: 21:18 min. On a boring, rainy weekend, Charlie convinces Alan to ride with Jake and him to Las Vegas. Apprehensive about his upcoming colonoscopy, Alan agrees that the diversion will be good for him. After Alan packs numerous suitcases, and the guys are ready to leave, Jake becomes physically ill. Judith visits the house and then forbids Alan to take Jake anywhere without her permission. Alan and Charlie want to defy Judith, but when Jake becomes ill again, the two brothers realize they must be responsible adults and stay home.
Original air date: 02/14/2005 Runtime: 21:20 min. Judith takes a vacation and leaves Jake with Alan. But then Alan finds out he's being audited by the Internal Revenue Service. Burdened with this last-minute misfortune, he's forced to leave Jake in Charlie's irresponsible hands and hopes that his brother can get Jake to school.
Original air date: 02/21/2005 Runtime: 21:18 min. While in a precarious position with a woman, Charlie injures his back and won't let Alan--a chiropractor--help him. After Alan drives Charlie to the doctor's office, Charlie is surprised to learn that his physician died four years ago, and a beautiful female, Dr. Michelle Talmadge (ALICIA COPPOLA - "Bull"), has replaced him. Meanwhile, Berta teaches Jake a lesson.
Original air date: 03/07/2005 Runtime: 21:28 min. Charlie masquerades as a homosexual so that Eric (DAVID STARZYK), the gay owner of an advertising agency, will continue to give Charlie more jingles to write. Charlie convinces Alan to pretend to be his gay partner and attend a party hosted by Eric. At the party, Charlie is immediately attracted to Pamela (LUCY LAWLESS - "Xena: Warrior Princess")--who is convinced Charlie is gay even after he confesses the truth. But the pressure of trying to prove his heterosexuality to Pamela proves too much for Charlie to overcome.
Original air date: 03/21/2005 Runtime: 21:28 min. While at a coffee shop, Alan and Charlie encounter Sherri (recurring guest star JERI RYAN - "Boston Public"), a woman who once dated Charlie just so she could have sex with him. Alan is enchanted with her beauty, so Charlie encourages Alan to ignore his memories of teenage rejection and ask her on a date. Alan's befuddled approach is surprisingly successful because Sherri no longer wants shallow, purely sexual relationships and is hoping to experience a deeper, more caring connection. Unfortunately, during his date with Sherri, Alan can't seem to get thoughts of Charlie with Sherri off his mind.
Original air date: 04/18/2005 Runtime: 21:28 min. Evelyn harasses Charlie for not calling her, and Judith bills Alan for an expensive pair of tennis shoes she bought Jake. Unable to express the anger they have towards the women in their lives, Charlie and Alan lash out at each other. Rose--with her questionable background in behavioral psychology--tries to help the two brothers sort out their feelings.
Original air date: 05/02/2005 Runtime: 20:53 min. While scanning the obituaries for potential property listings, Evelyn discovers that her second husband, Harry, has died. Although pleased that Alan agrees to attend the funeral with her, she's furious to hear that he had stayed in contact with Harry over the years. Evelyn then reveals to her sons that she didn't actually leave Harry, but that he left her--for a younger woman. Charlie and Jake also attend the funeral. And Evelyn learns a surprising new detail about her ex-husband.
Original air date: 05/09/2005 Runtime: 21:23 min. After Evelyn gives Alan a loan so he can purchase a new Porsche, Charlie informs his brother that Alan has sold his soul to the devil. Evelyn proves Charlie is right when she coerces Alan to go on a double date with Trudy (CHLOE WEBB - "China Beach, " "Sid and Nancy")--whose father Evelyn wants as a boyfriend. But Evelyn and Trudy's dad never shows up at the restaurant, leaving Alan alone with Trudy. And Alan learns things about his date that he'd rather not know.
Original air date: 05/16/2005 Runtime: 20:47 min. When Evelyn learns that Jake spent his entire spring vacation with his other grandparents, she pressures Alan into letting Jake stay with her for a night. Concerned that Evelyn will destroy Jake's life the way she destroyed theirs, Alan and Charlie grudgingly take a resentful Jake to Evelyn's home and quickly flee to Charlie's favorite bar. There, amid a bevy of sexy female volleyball players, Alan easily forgets about his son's miserable circumstance.
Original air date: 05/23/2005 Runtime: 20:34 min. Charlie has sex with a gorgeous young woman, Natalie (KAREN TRELLA), without realizing she's married to an elderly man, Norman (ORSON BEAN - "Dr. Quinn, Medicine Woman"). At school, Jake is required to give a report to his fifth-grade class about his weekend. He recalls that he was eating breakfast when an old man came to the house looking for his wife. From there, Jake's perspective of the weekend's events departs from what really happened at the Harper home.