
After falling off the roof, Alan needs Charlie's help in looking after Jake, which interferes with Charlie's social life.
Guest Stars:
Kimberly Oja, Sandra Purpuro
Jake gets suspended from school after drawing an offensive picture of a girl in his class that has large breasts. Meanwhile, Charlie is asked to watch over Alan's chiropractic office after pulling an all-nighter.
Guest Stars:
Candace Kita, Stephanie Erb, Diane Sellers, Lincoln Kennedy, Anna Pheil
Alan has been dating a lot, and Charlie soon finds out that it has been one woman - his ex-wife, Judith. He tries to stop Alan, and even brings Rose, Evelyn and Berta to interfere - but Alan ignores them all.
Guest Stars:
Melanie Lynskey
Berta causes tension between Charlie and Alan, when she temporarily moves in with them
Charlie learns he can't be in a long-lasting relationship, becuase of unresolved issues he has with his mother. Jake asks Charlie for advice about a girl at school.
Guest Stars:
Melanie Lynskey, Natalie Zea
Ignoring Alan's warnings, Charlie continues to date Isabella until she threatens to put a curse on his manhood.
Guest Stars:
Jodi Lyn O'Keefe
Charlie wakes up with Rose the morning after her birthday party. Her irate father comes to ask Charlie about what the future holds for him and Rose, but the unexpected happens when Evelyn shows up.
Guest Stars:
Melanie Lynskey, Martin Sheen, June Squibb
Charlie tricks Jake into taking ballet lessons, so he can get close to the teacher.
Guest Stars:
Emmanuelle Vaugier
One of Charlie's elderly neighbors tries to seduce Alan, while Charlie tries to stop Jake from giving money to a televangelist.
Guest Stars:
April Bowlby, Cloris Leachman, James Edson, Glen Walker
Charlie helps Alan with his obsession of always having to get approval from the women in his life.
Guest Stars:
Jennifer Ann Massey, Aja Evans, Rebecca McFarland
Alan starts dating a woman with a Martha Stewart complex. Before long she's running the house with an obsession for perfection.
Guest Stars:
Josie Davis
Charlie sees a therapist to learn how to deal with Alan's emotional insecurities.
Guest Stars:
Andrea Bendewald, Valerie Azlynn, Stephanie Reibel, Jane Lynch
Charlie finds himself in a relationship that is not based on sex.
Guest Stars:
April Bowlby, Emmanuelle Vaugier
Charlie arranges a romantic date with Mia in the hopes of consummating their relationship. Alan begins to date Charlie's most recent ex-girlfriend.
Guest Stars:
April Bowlby, Emmanuelle Vaugier
Charlie has trouble keeping up with Mia's healthy lifestyle, so he begins to sneak beers, cigars, and burgers behind her back. When Mia finds out what he was doing, Charlie has to decide if he is truly in love with her or just whipped.
Guest Stars:
Melanie Lynskey, Jackie Debatin, Rod Britt, Nanci Christopher, J.D. Walsh
Alan has trouble deciding if he should bring his younger girlfriend to Jake's birthday party to meet his mom and his ex-wife. Rose tries to get her boyfriend to act more like Charlie.
Guest Stars:
Melanie Lynskey, April Bowlby, Hugh Holub, Brian Thomas Smith, Terry Shusta
Charlie is nominated for an advertising award, but he decides to boycott it because his arch nemesis always wins. The rest of his family tries to trick him into going. Rose is having relationship problems with Gordon and seeks help from Charlie.
Guest Stars:
Alan starts to have financial problems when he starts paying for his girlfriend's bills, so Charlie tries to get him to break up with her. Meanwhile, Judith is after Alan because he is late in paying his alimony check.
Guest Stars:
April Bowlby, John Mendoza
Charlie is surprised to find out that Kandi has been living with them for the last three weeks. Alan is having a tough time helping Kandi earn a living. Charlie has lost his sense because of the dry-spell he is going through.
Guest Stars:
April Bowlby, Gail O'Grady, Diane Delano
Alan tries to win Kandi back. Meanwhile, Charlie starts to sleep with her mom, Mandi, and Judith gets set up with her father, Andy.
Guest Stars:
April Bowlby, Kevin Sorbo, Gail O'Grady
Jake’s teacher has a meeting with Alan and Judith to discuss the lack of interest Jake has at school. Alan starts to fall for Francine, in a platonic way, because he is tired of the lack of intelligent communication he has with Kandi. Charlie helps Jake audition for his school musical.
Guest Stars:
A girl from Jake’s school invites him to his first boy-girl party. Charlie and Alan help him get ready for it by giving him advice. Alan and Charlie get nostalgic and remember their first boy-girl party.
Guest Stars:
Ralph Cole Jr., Stephanie Brown
Mia comes back to town with her dance troupe and invites Charlie to her performance. At first, he decides not to go and tries to convince Alan that he no longer has feelings for her. He goes to the see the performance and Mia explains that she wants some of Charlie’s sperm. Charlie responds by asking Mia for something.
Guest Stars:
Charlie and Mia start making their wedding arrangements. Things begin to fall apart when their two families meet each other. They eventually decide on a small ceremony in Las Vegas.
Guest Stars:
Holland Taylor, Melanie Lynskey, April Bowlby, John Vance, Emmanuelle Vaugier
Melanie Lynskey, Loren Lester, Robert Clotworthy, Jon Lovitz, Theresa Adams
April Bowlby, Julia Campbell
Conchata Ferrell, April Bowlby, Cheyenne Casebier, Maria Tornberg, Raymond Ma
16 Episodes