After the death of Charlie Harper, Alan faces the reality of moving out of his brother's beach house - until he meets a depressed Internet billionaire whose wife just left him.
Walden buys Charlie's house and hires Berta as his live-in housekeeper, forcing Alan to move back in with his mom. However, Alan sees an opportunity to come back when Walden asks for advice about getting his wife back.
Alan begins working on getting Lyndsey back, but his days at Walden's place may be numbered after Walden hooks up with Charlie's gold-digger ex girlfriend, Courtney.
Alan convinces Walden to see Charlie's old shrink after he gets his divorce papers from Bridget, but his spirits are soon lifted after he meets a lesbian who looks like her.
Walden hires Evelyn as his interior decorator, but Alan is convinced that she just wants to take advantage of him sexually. Meanwhile, Alan inherits Charlie's journal, and Jake has a crush on his tutor, but she has a crush on Walden.
Still emotional after Charlie's death and jealous over Walden's ability to pick up hot single women, Alan takes a break from reality and channels his inner Charlie.
Upon his return from the "stress clinic," Alan finds out that Jake got his girlfriend pregnant, Walden and Lyndsey are sleeping together, and he has to move out immediately.
After Jake talks Walden into asking out a woman he meets at a supermarket, Alan considers hocking Walden's incredibly expensive wedding ring to get out of debt.
Walden's mother arrives for Christmas and Alan is smitten with her, even as she reveals a secret about a brother from Walden's past that sends him into a downward spiral.
When Bridget and Walden's mother try to take control of Walden's company, Walden puts Alan on the board. But can he be trusted once Walden's mother gets to him?
Alan and Lyndsey introduce their mothers to each other, while Walden spends the night hanging out with Jake and Eldrige since Zoey is still out of town.
Zoe is upset when she finds out that Bridget is a business partner in Walden's latest venture, while Alan and Lyndsey have an awkward dinner with their moms, who are now lovers and are planning to move in together.
Walden's commitment is tested when Zoey and her daughter come to live with him. Meanwhile, Alan gets more than he bargained for when he moves in with Lyndsey.
Alan decides to take advantage of the guilt felt by his family and Walden after his heart attack, but Zoe knows that he's just milking it and sets out to prove it.
Jake and Eldridge make an important decision about their future after they graduate from high school and get fired from their jobs at Walden's new company.
