Walden dates a hot 22-year-old woman, but finds himself more attracted to her worldly grandmother. Meanwhile, Alan and Jake go on a father-son bonding trip.

When Walden encourages a depressed Alan to update his look and start dating again, Alan faces a moral dilemma when he attracts a married woman.

Alan has trouble coping when Lyndsey dumps him and Walden must find a way to help him get back on his feet.

When Jake cheats on his girlfriend with her 18-year-old daughter, Alan and Walden get caught in the crossfire.

Walden and Alan try to cheer up a lonely Herb, but end up partying a little too hard.

Following a fight with Walden, Alan moves in with Herb.

When Walden runs into his ex-wife at a high-end singles mixer and they talk about getting back together, Alan worries that she's not good for Walden.

Walden, depressed about being single on Valentine's Day, tries to convince Kate to give him another chance. Meanwhile, Alan's Valentine's Day plans take a turn for the worse.

Alan has concerns when Jake brings his 36-year-old girlfriend home for a visit. Meanwhile, Walden tries to keep a secret from Alan.

Alan and Lyndsey's relationship is strained when he won't give her a key to the beach house. Meanwhile, Walden, Alan, Billy and Herb commiserate about women and relationships.

Walden and Alan go to Kate's fashion show in New York so Walden can tell her the truth about his identity.

Using Walden's money, Alan invests in Kate's fashion line. Meanwhile, leading a double life starts to take its toll on Walden.

Walden juggles having two identities - rich man and poor man - and Alan finds himself alone at Christmas.

Alan helps Walden create a new identity in order to find a woman who isn't just after his money.

Alan's smokin' hot, famous ex-wife, Kandi, wants him back. Meanwhile, Berta isn't interested in celebrating her birthday, so Walden helps make it special.

Alan is hesitant to make a serious commitment to Lyndsey but gets inspiration from an unlikely source. Meanwhile, Walden enjoys being a boy-toy for a rich older woman.

Tired of the complications of a traditional relationship, Walden hires an actress to play the part of his girlfriend. Meanwhile, Jake and Missi plan a rendezvous at the beach house.

Walden has to choose between Rose and Zoey.

Despite Alan's warnings, Walden starts dating Rose.

Walden starts to feel his age when a friend's daughter comes to town.

Alan and Lyndsey decide to spice things up in the bedroom.

Following his break-up with Zoey, Walden has a breakdown.

Walden plans a big surprise for Zoey's birthday.