Whitney arrives in New York City during fashion week just in time to start her career with Diane Von Furstenberg. When she's invited to an "uptown" dinner party she discovers her "downtown" boyfriend wants no part of that world.
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Whitney's world is turned upside-down, when a boy from her past shows up to warn her that Jay has been fooling around. Olivia decides to make a project out of making Whitney her friend.
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Whitney gets mixed signals from Jay. Erin's new boyfriend comes to visit and Whitney realizes it's time to find her own apartment. Olivia grows frustrated when Whitney refuses to listen to any of her advice.
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Whitney dates a new guy and Jay gets jealous. Erin thinks things are moving too fast with Duncan when he suggests moving in. Jay confesses to Adam his true feelings about Whitney.
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Adam lets loose while his girlfriend Allie is out of town, but when she hears he kissed another girl from Whitney and the others, Adam finds himself in hot water.
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Allie breaks down after a face-to-face run in with the girl who claims she kissed Adam, but Adam sticks to his story to win Allie back. Whitney gets upset with Jay for taking Adam's side, and Olivia and Nevan judge the scandal.
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Kelly Cutrone accuses Allie of being too skinny, and Whitney finds herself caught in the middle. Erin runs into an ex-boyfriend, and old feelings begin to return.
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Olivia invites Jay's band to perform at one her charity events but her plan backfires, leaving Whitney and Olivia at odds. Erin's relationship with Duncan is threatened by her renewed feelings for her ex-boyfriend JR.
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Adam kicks Jay out of his apartment so Allie can move in permanently and Jay asks Whitney if he can live with her.
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When the gang goes to Miami for the weekend, Jay runs into his ex-girlfriend Danielle, and Whitney wonders if the rumors about them might be true after all.
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Whitney discovers that Jay's mysterious night out was spent with his ex-girlfriend Danielle. Olivia steals all the credit from Whitney when they style an ELLE cover shoot and Allie decides that she needs space from Adam.
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When Jay finds out he's going on tour, Whitney isn't willing to give up on the relationship, but when Jay doesn't give her a choice their relationship ends in a tearful goodbye.
