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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.
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.
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.
In New York, things change overnight. Now Whitney is taking a chance on her dream of becoming a designer, under the critical eye of Kelly Cutrone. She's single, dating, and settling in to a new place in NYC's West Village.