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- After Jake flips off his teacher, Alan and Judith move to punish him. Charlie, meanwhile, has other plans for Jake's teacher. Chaos ensues when Jake discovers the relationship and the increasingly overbearing Miss Pasternak tells Charlie she believes God brought them together.
- 2003–201522mTV-147.3 (1.4K)TV EpisodeEvelyn announces she is receiving an honor from the real estate industry and that Charlie and Alan will host a party in her honor. Mayhem ensues when Berta and her sister agree to cater the event, but sibling rivalry takes center stage.
- 2003–201522mTV-147.8 (1.4K)TV EpisodeA freak food-flinging accident leaves Alan with impaired vision, which doesn't bode well especially when he draws a liking to one of Charlie's exes.
- An old classmate is in town while Charlie and Alan spar over whom she likes more.
- 2003–201521mTV-147.8 (1.4K)TV EpisodeAfter one of her ex-husbands dies, Evelyn summons Alan, Charlie, and Jake to the funeral, where Charlie takes a keen interest in the widow.
- 2003–201520mTV-147.6 (1.6K)TV EpisodeSeeing Judith's new look and boyfriend prompts Alan to realize that if he wants to get back into the dating scene, he will need to change his look also.
- 2003–201521mTV-148.4 (1.9K)TV EpisodeCharlie's old flame Jill visits and has really changed: she had an operation and is now called "Bill." Before Charlie can adapt, Evelyn meets and starts dating Bill.
- 2003–201520mTV-147.9 (1.6K)TV EpisodeCharlie is offended when Alan chooses their married, responsible cousins as Jake's guardians.
- Charlie is having some friends coming over to his house to have a gathering but Alan is not invited. Things got worse when Alan is also not invited to Judith's party even though her guests are Alan's friends.
- Charlie is dating a self-assured woman who plays hard to get, easily dismisses him, and he finds it disarming. Rose gets Charlie to see that his new lady-friend, Sherry, is in his head because she is just like him; a self-centered, manipulative, narcissist. Charlie debates breaking it off. Alan and Jake fiercely battle wills over Jake doing his homework.
- 2003–201521mTV-148.6 (2.5K)TV EpisodeBerta brings her 16-year-old granddaughter to work, which poses issues for the men.
- 2003–201522mTV-148.2 (1.5K)TV EpisodeIt's the week of hell as Judith's out of town, Alan's got Jake, and nothing seems to be going right.
- Charlie is sure he isn't ready for fatherhood after a year of trying to raise Jake, so he opts to have a vasectomy. But when the doctor performing the procedure keeps getting calls from his wife -- who's about to give birth -- Charlie starts to think about what fatherhood might entail and likes the idea, provided he still has his vital organs intact (in more ways than one).
- 2003–201522mTV-147.7 (1.3K)TV EpisodeAfter it's revealed Alan and Judith have been trying to reconcile, Charlie, Evelyn, and Rose vie for the role of spoiler.
- 2003–201521mTV-147.5 (1.7K)TV EpisodeCharlie and Evelyn date members of the same family.
- 2003–201521mTV-148.3 (1.5K)TV EpisodeJake recounts his weekend in which Charlie's latest fling is with a woman who turns out to be married to a now very angry old man.
- Alan is hurt when he finds out that Judith is seeing Jake's pediatrician; meanwhile, Evelyn tries to find out why Charlie hates her.
- 2003–201522mTV-148.0 (1.4K)TV EpisodeAlan gets carried away with a woman he met at the supermarket, and it's up to Charlie to talk some sense into him while shielding Jake and Judith from what's going on.
- 2003–201522mTV-147.7 (1.9K)TV EpisodeCharlie and Alan go out drinking. Alan tries to reconcile with his wife. After that fails, they decide to confront the root of their issues, their mother.
- 2003–201521mTV-147.5 (1.5K)TV EpisodeJake plays electric guitar all day long and doesn't want to do anything else. Alan and Charlie can't figure out why. Jake refuses to discuss anything with anyone, including his grandmother and even a psychologist.
- Charlie's Satan-worshiping girlfriend has a knack for the supernatural, and seems to be the cause of some strange happenings around the Harper house.
- 2003–201522mTV-147.6 (1.3K)TV EpisodeCharlie has to decide whether he can really commit to a serious relationship with Mia, especially when sex is currently off the agenda. Unsurprisingly, his suggestion that he sleep with other women in the meantime falls on somewhat stony ground.
- 2003–201522mTV-147.6 (1.4K)TV EpisodeRose intervenes after Alan and Charlie come to blows over some of their unresolved issues.
- Charlie's accountant Stan tries to make Charlie understand his desperate financial situation.
- 2003–201519mTV-148.1 (1.7K)TV EpisodeJudith's sister Liz visits for Jake's birthday.