Walden meets another young, drunk girl and drives her home where her grandmother receives them. An unexpected turn of events make Walden find her attractive while Jake gives Alan big news about his brand new job.
Alan tries to get over the break up, and Walden decides to help him with that and borrows his credit card to him. Alan gets a change of looks and meets a new lady "friend".
After some time of thinking and decision making Lindsey decides to break up with Alan leaving him devastated. After a short period of denial Alan finally accepts the break up and takes his own little revenge on her.
Jake gets caught cheating on his girlfriend, Tammy with her own daughter.
Walden and Alan try to keep up as Herb goes on a wild party binge at the beach house.
When Alan and Walden have a falling out, Alan has no choice but to seek refuge with Herb.
Walden attends a singles mixer for rich people and runs into Bridget. Alan gets worried when they begin talking about getting back together.
Valentine's day is approaching, and Alan wants to make it special for Lindsay. Unfortunately, his plans go awry at the last minute. Kate is back in town and wants to meet up with Walden, but can he convince her to take him back?
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.