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Walden ignores Alan's warnings and starts dating Rose (Melanie Lynskey).

Walden must choose between Zoey and Rose.

When Walden gets tired of the complications that come with a traditional relationship, he hires an actress to be his girlfriend; Jake plans a rendezvous with Missi (Miley Cyrus) at the beach house.

Alan feels reluctant to make a commitment to Lyndsey, but an unexpected source inspires him; Walden enjoys being the boy-toy of a wealthy older woman.

Alan's famous ex-wife, Kandi, wants to reconcile; when Berta isn't interested in celebrating her birthday, Walden tries to make her day special.

Alan invests Walden's money in Kate's fashion line; leading a double life takes its toll on Walden.

Alan and Walden go to Kate's fashion show in New York, so Walden can reveal 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.