New York welcomes Brad with a week full of fashion frenzies and family affairs. After arriving in the Big Apple, Brad puts his styling skills to work at a shoot for the luxury brand website, Gilt Groupe. Another outfit later, he's off to InStyle to discuss an upcoming column and then to Details Magazine where Brad pitches his ideas for a possible photo spread. As if that's not enough, Brad hires a much-needed personal assistant, Lindsay, and Brad's mom and sister arrive in NYC. For the first time in ten years, they will meet Gary's family. In the midst of this chaotic trip, Brad is hit with vital news that could completely turn his career upside down.