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When Andy's attempt to help Wendy with her singing career backfires, she decides to give up her dream entirely. Meanwhile Jessica fools herself into thinking office hunk Milo is not only cute, but also smart and witty.
The co workers are eavesdropping on Jessica's therapist neighbor, who describes her 'cold'. So, Jessica desperately tries to change her ways. Meanwhile Andy hits on Dina, one of the therapist's patients, knowing that she'll begin a relationship with anyone providing he doesn't tell her he loves her.
Freddie Pickering, kooky heir to the Pickering legacy, promotes Andy and has him join his life of wealth and debauchery. As this creates a rift between Andy and his friends, he proposes to take them along on a trip to Rio.