Alan is upset when he discovers that Lyndsey broke up with Larry and kept this information from him. When Walden’s masculinity is questioned he decides to prove he is a real man.
Walden and Alan throw a bachelor party for Marty once he proposes to Evelyn.
Walden is feeling frustrated because Nicole has no time for him due to a software project, so he offers to help her with it. Larry convinces Alan to go on a blind date, which Larry arranges.moreless
Alan gives Jenny relationship advice and Walden enters into a new project with a former employee.
Jenny needs Walden’s help in getting a second date and Alan finds trouble with his girlfriend’s ex-wife.
Walden ends up on a date with a clumsy woman which extends his time with her. Alan finds himself involved with a woman who shares too much information with him.
Walden finds himself in danger and must turn to Rose for help as a result if the affair between Alan and Lindsey.
Walden and Alan plan a double date with two attractive women, but Lyndsey gets jealous and ruins the evening.
Alan persuades Walden into inviting Lynda Carter over to dinner.
Alan spends time with Lyndsey’s boyfriend in hopes of discovery why Lyndsey likes him so much. Walden encourages Jenny to take her acting career more seriously.
Jenny moves into Evelyn’s home because of Walden’s feelings. Alan hooks up with Lyndsey even though she is seeing another man.
Jake gets caught cheating on his girlfriend, Tammy with her own daughter.
Walden attends a singles mixer for rich people and runs into Bridget. Alan gets worried when they begin talking about getting back together.
Lyndsey's miffed that she doesn't have a key to the beach house. Meanwhile, Walden, Alan, Billy, and Herb share stories about women.
Waldentakes Alan along to New York to see Kate at her show and reveal his true identity.
As Alan gets increasingly comfortable living in the beach house. Walden wants to invest in his girlfriend Kate's fashion career, without her discovering that he is billionnaire Walden Schmidt rather than broke Sam Wilson, as he has led her to believe. The stress of this deception begins to affect Walden's health.moreless
Walden is struggling to keep his two identities straight and Alan is home alone on Christmas.
Alan helps Walden create a new identity in order to find a woman who isn't just after his money.
Alan's ex-wife, Kandi wants him back and Walden helps Berta celebrate her birthday!
Lyndsey wants a serious commitment from Alan. Walden hides his identity to be with a rich older woman who uses him as boy-toy.
Walden hires an actress to play as his girlfriend. Missi returns to the beach house and so does Jake.
Zoey comes back into Walden's life, which forces him into a making a deision between her and Rose.
Walden starts dating Rose regardless of Alan's warnings against it.
Missi, the daughter of a friend of Walden's, visits at the same time that Jake is on leave.
Lyndsey and Alan try to add a little excitement to their love life.
Walden, still reeling from his break-up with Zoey, buys a dog.
Walden rushes to plan a surprise birthday party for Zoey.