Walden's proposal on Zoey's birthday does not go as planned.
Walden struggles with his feelings after his breakup with Zoey and takes it out on his friends and family.
Alan and Lyndsey's love life becomes stale, so they agree to participate in each other's fantasies, which for Lyndsey involves Walden.
A friend's daughter comes to visit Walden and makes him feel old when she tries to set him up with her mom.
Walden takes Lyndsey up on her offer to set him up with some of her friends. The results are disastrous, so he decides to be alone until Rose appears.
Walden faces a dilemma, choose Rose who just moved in, or Zoey, who wants him back.
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.
Lyndsey draws a line in the sand regarding her commitment to Alan and he struggles with his decision. Walden becomes a boy-toy.
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 helps Walden create a new identity so he can avoid women who are only interested in his money.
Walden juggles having two identities - rich man and poor man - and Alan finds himself alone at Christmas.
Kate is ready to give up her dream of designing clothes so Walden devises a plan to have Alan invest in her future using Walden's money. However, the pressure of living a lie is wreaking havoc on Walden physically.
Walden and Alan go to Kate's fashion show in New York so Walden can tell her the truth about his identity.
Alan is faced with relationship trouble when he does not give Lyndsey a key to the beach house; Walden, Alan, Herb and Billy commiserate about relationships.
Alan has concerns when Jake brings his 36-year-old girlfriend home for a visit. Meanwhile, Walden tries to keep a secret from Alan.
Walden is surprised when he hears from Kate just before Valentine's day and Alan convinces him to not take no for an answer. Meanwhile, Alan's elaborate Valentine's Day plans go awry, painfully awry.
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.
Alan finally gets on Walden's last nerve and after a fight, Alan moves out and stays with Herb.
Walden and Alan try to cheer up a lonely Herb, but end up partying a little too hard.
When Jake cheats on his girlfriend with her 18-year-old daughter, Alan and Walden get caught in the crossfire.
Alan's world spirals downward when Lyndsey decides their relationship is over. Walden looks for a solution to free himself from being the sole person in Alan's life.
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.
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.