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Alan convinces Charlie to date more respectable women and sets him up with a judge. Charlie and Alan go on a double date but find out the waitress is an ex of Charlie's.
Charlie acts strange after spending the evening with Evelyn; a woman Alan sleeps with begins acting strange herself.
Jake gets ready to start junior high school as Alan and Charlie take him shopping. The two brothers manage to get themselves in trouble.
Evelyn gets a new boyfriend, Teddy, who bonds with Charlie and Alan over a trip to Vegas. The boys confront their feelings about their mother's dating.
Charlie is shocked when the young handyman working on his house beats him out for Chloe. Alan has no sympathy for him.
Alan asks Charlie to help Jake with his book report so that he can go to the DMV. Charlie ends up taking Jake to the race track while Alan gets conned at the DMV.
Alan and Charlie re-examined their sexuality after Alan becomes friends with Greg, a homosexual. Jake has a crush on Greg's daughter.
Alan looks forward to Judith's wedding while Charlie and Myra continue their relationship.
Alan is thrilled to give Judith his last alimony check; Charlie takes Herb's sister, Myra, out for a date and they bond over their hatred of Judith
Alan tries to bond with Jake when he realizes his acting career is over; Kandi pursues an acting career