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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
After Evelyn confides in Alan and Charlie about how she doesn't want to die like her friend no loved ones at her funeral, the boys convince her this could be her one day.
Charlie's young, hot girlfriend takes him to a new club. Charlie takes Alan with him and they're shocked to learn they're considered old.
Rose is moving to London and Charlie is surprised by his reaction to the news; Alan lies to a woman he met online
Charlie sets up Alan with the new neighbor Danielle but gets jealous when the two bond
When Jake tells Charlie and Alan he heard his mother having sex with Herb, it conjures up a repressed memory of Charlie's and he seeks help from Rose
Berta discovers that Alan has been secretly dating her daughter, Naomi.
Charlie's friends and family interrupt his Christmas date. When Evelyn finds out who the date is, she tries to push them apart.
Fearing he'll get rid of one of them, Berta and Lydia fight to stay; Kandi tries to stop Alan from selling their condo.
Charlie reaches the breaking point with putting up with Alan's mooching during a double date; Jake is left home alone for the first time
Alan suffers from insomnia and visits his psychiatrist that tells him it's due to his jealous towards Charlie
Berta's daughter is pregnant and Berta drags Charlie with her to confront the baby daddy; Alan shows his fetish for pregnant women while they're gone
Charlie is dating a woman whose personality and life are similar Evelyn's, his mother
Alan is excited by the prospect of Judith remarrying and ending his alimony payments. Alan gets Charlie to help him when he thinks the marriage might not go through because of Jake disliking her fiance.
Alan tries to hire his ex-lawyer to help him win custody of his dog from Kandi
Charlie tries to surf to impress Dottie, but nearly drowns when he thinks he sees his dead father
Charlie tells Alan why he didn't marry Mia; Charlie and Alan deal with their noisy neighbor, Steven Tyler
With Alan out of the house, Charlie returns to his bachelor lifestyle until Alan returns, having been divorced from Kandi already.