"That Old Hose Bag Is My Mother" - Season 2

Evelyn buys Alan a new sports car, causing Charlie to claim that his brother has sold his soul to the Devil. The next day, Evelyn extracts payment by insisting that Alan go on a blind double date with her, her new beau and his daughter. At the restaurant, Alan learns that his mother and boyfriend will not be able to join them because there was a mix-up between his heart medication and Viagra and she didn't want to "waste it." As a result, Alan is left to deal with the daughter (Chloe Webb), who is on a weekend pass from a rehab center and still has some loose screws. Alan eventually gets her back to the beach house only to have her drive off in his new sports car and become the object of a televised high-speed car chase.

"A Sympathetic Crotch to Cry On" - Season 2

Evelyn reads in the obituaries that her second husband Harry has died. They all attend the funeral, including Jake who is excited at the opportunity of seeing a "dead guy." Meanwhile, Charlie is excited by the opportunity of a newly single widow, and Alan is just happy to pay his respects to Harry.

"I Always Wanted a Shaved Monkey" - Season 2

Rose tries to help the brothers sort out their feelings, when Charlie and Alan take their personal frustrations out on each other.

"A Low, Guttural Tongue-Flapping Noise" - Season 2

After Charlie takes Alan to an eye doctor, they end up at a cafe where they bump into Charlie's ex-girlfriend, Sherri (Jeri Ryan). Alan takes an interest in Sherri, and decides to ask her out. The problem is that Alan can't get over Sherri's relationship with Charlie.

"It Was "Mame," Mom" - Season 2

Charlie is invited to a party hosted by a gay ad-executive named Eric, so Charlie asks Alan to pretend that he's his life partner. While at the party, Charlie meets Eric's ex-wife Pamela, and tries to sleep with her without Eric finding out.

"Woo-Hoo, A Hernia-Exam!" - Season 2

After Charlie has back pain, Alan decides to take him to the hospital after refusing his help. While there, Charlie can't stop hitting on the doctor who is examining him. The only problem is that he has a history with her that he can't remember. Berta is fed up with Jake's inability to use the bathroom properly, so she decides to make him clean it until he learns.

"Can You Eat Human Flesh with Wooden Teeth?" - Season 2

When Judith decides to take a vacation, the brothers have to take care of Jake during the week. Alan finds it challenging, and even forgets to pick up Jake from soccer practice. When Alan finds out that he has to go to the I.R.S. because they're auditing him, he forces Charlie to take care of Jake, and Charlie doesn't do any better than Alan.

"Smell the Umbrella Stand" - Season 2

Alan starts to worry about a proctology examination that he is facing, and to get his mind off it Charlie suggests they go to Las Vegas.