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Charlie sleeps with a woman (Karen Trella) who turns out to be married to an old man, Norman (Orson Bean), that seems very much like an older Charlie. Meanwhile, Jake has to read a paper to his class.
After finding out Jake spent Spring Break with Judith's parents, Evelyn demands that Jake spend the night at her place. Though Alan and Charlie dislike the idea, they drop him off and head to the bars to drink away their concerns.
Evelyn buys Alan a sports car and, as Charlie warns him, expects a favor in return. Evelyn makes Alan go on a blind double date with her.
When Evelyn finds out from the obituaries that her second husband, Harry, has died, she and the family attend the funeral. Charlie ends up hitting on Harry's newly single widow, Jake is excited to see a "dead guy" and Alan is happy to pay his respects.
When Charlie and Alan get into a fight, Rose tries to step in and mediate.
After Charlie takes Alan to the eye doctor, they end up at the coffee shop where they run into Charlie's ex, Sherri (Jeri Ryan). Alan ends up asking out Sherri, but can't get over her prior relationship with Charlie.
Charlie is invited to a party hosted by a gay ad-executive, Eric (David Starzyk), so Charlie brings Alan to pretend to be his life partner until he meets Eric's beautiful ex-wife.
After Charlie has back pain, Alan takes him to the hospital. Charlie ends up hitting on the doctor, who he's already dated. Berta is fed up with Jake's continuous mess in the bathroom.
When Judith decides to take a vacation, Alan has to take care of Jake during the week and finds out it's more work than he thought. When his IRS audit forces Charlie to take care of Jake, he doesn't do much better.
Alan starts to worry too much about a medical procedure he's about to get, so Charlie tries to distract him by going to Vegas.
Charlie and Alan throw out Evelyn when she insults the way Alan is raising Jake. When their mom ends up the hospital, they're not sure if it's real or a ploy to get back their affection.
Alan invites Judith to stay at Charlie's place after an earthquake. When Judith has a date, Alan becomes very jealous and begs Charlie to find him one too.
Alan meets up with an old nerdy classmate he was friends with who has now become a beautiful woman. Alan gets very jealous when she seems to be showing more interest in Charlie.
After getting rejected at the bar, Charlie learns about a website that exposes his lifestyle. Charlie sets to find out who created the site, making amends with all girls he hurt.
When Charlie has to write a theme song for a comic book, Oshikuru, Jake is a fan of, he tries to enlist his help. Meanwhile, Alan finds out more about Rose as he hangs out with her.
When Charlie leaves the house to avoid a date he can't stand, he ends up at the coffee shop where he runs into his old girlfriend, Lisa (Denise Richards), who is now a divorcee with a baby. Jake tries to justify to his father why he isn't doing well in school.
When Alan meets Nancy (Kelley West) at the grocery store, she fulfills all his fantasies, forcing Charlie to take care of Jake while he's distracted. After knowing Nancy for just a few days, Alan decides to ask her to marry him making Charlie to try and stop him, even getting Evelyn to help.
Charlie and Alan hire Berta's sister to cater a party their mom forces them to have for her.
Alan denies having shoplifted a toy as a kid for fear he has a darkside until Charlie finally admits he planted the toy on Alan, changing his life forever.
Charlie meets his match when he falls for a woman, Sherri (Jeri Ryan), that's better at playing hard to get than he is.
Alan gets jealous when Jake is impressed with his mother's new boyfriend, Dr. Melnick. Meanwhile, Evelyn borrows Charlie's car to impress her client, a Saudi prince.
When Jake gets in trouble for giving his teacher the middle finger, Charlie tries to help by romancing his teacher.
Judith is dating Jake's pediatrician, Dr. Melnick (Ryan Stiles), which initially upsets Alan until Charlie points out if they get married his alimony payments end.
When Alan learns that Charlie belongs to an exclusive men's club that includes celebrities such as Henry Dean Stanton, Sean Penn and Elvis Costello, Alan wants in.