When Alan discovers that Charlie is part of an exclusive men's group, he desperately tries to join them. But when Alan is finally part of the group, he ends up getting on everybody's nerves.
Alan freaks out when he finds out that Judith is dating Jake's pediatrician. Evelyn doesn't know why Charlie doesn't seem to like her.
When Jake faces trouble with his teacher Delores, Charlie steps in to save the day. But his attempts to charm Delores in order to forgive Jake backfires.
Alan is annoyed when Jake is impressed with his mother's wealthy new boyfriend. When Evelyn borrows Charlie's car for a business deal, she ends up forgetting her bra there.
Charlie is facing trouble when he dates a new woman who is more challenging that he thought. Alan is trying to get Jake to do his homework.
Alan is upset with Charlie when he finds out that he made Alan take the blame for shoplifting when they were kids to get himself out of trouble
Charlie and Alan clash with each other when they are asked to host a real estate party in Evelyn's honor, while Berta seeks her sister's help with the party.
When Alan falls head over heels for a woman he just met, Charlie tries to step in and persuade him to not get carried away.
Charlie reconnects with an ex-girlfriend, who is now a single mom. Jake tries to figure out why he's not doing well in school.
Charlie is having a hard time with a new jingle he's working on. Alan and Rose are getting closer to each other, while Jake is stalling to finish his book report.
Charlie sets out to discover who is behind creating a website that is attacking him. Alan suspects that Judith wants to resume her relationship with him after overhearing her on Jake's webcam.
When an old classmate is in town, Alan becomes jealous of Charlie when she shows interest in Charlie, while in reality she has other plans in mind.
Judith ends up staying in Charlie's house after the plumbing in her house needs fixing following an earthquake. But when Judith goes out on a date, Alan's jealousy gets him in trouble.
When Evelyn makes fun of Jake after he passed his history test, Alan becomes furious and asks her to stay away from them, so Evelyn hatches a plan to get back at him.
When Charlie tells Alan to go together on a trip to Las Vegas to clear their heads, they run into various obstacles that get in the way of their plan. Meanwhile, Berta is having her own plans after they leave.
Charlie and Alan find themselves in over their heads when Judith is out of town for a week and they have to look after Jake while she's away.
Alan flirts with Charlie's doctor after he takes him to the hospital for his back pain. Berta is fed up with Jake's careless behaviour and decides to teach him a lesson.
Charlie asks Alan to pretend to be his boyfriend when he's invited to a party of a gay ad-executive. But when Charlie meets the host's charming ex-wife, he tries to convince her that he's straight
After an accident leaves Alan with an eye injury, he runs into one of Charlie's ex-girlfriends, and asks her out. But things don't go as he planned, when he has trouble dealing with her previous relationship with Charlie.
When Charlie and Alan clash with each other, Rose steps in to make them patch things up between them, as they end up discussing their unresolved issues.
When Evelyn's second husband dies, the family attend the funeral, where Charlie ends up flirting with the widow and Evelyn reveals to her sons an old secret.
Alan learns a tough lesson after he borrows money from his mother to buy a sports car, as she ends up making him pay a heavy price in return.
When Evelyn finds out that Jake spent time at Judith's parents, she asks him to spend the night with her. But the night proves to be a complete disaster, much to Alan and Charlie's delight.
Jake recounts a wild evening where Charlie had a fling with a married woman whose angry older husband catches them, and the husband ends up spending the night with Evelyn.