Welcome to The City! Whitney Port, who we've all come to know and love as Lauren's co-worker and friend on The Hills, has decided to leave her California life behind and risk it all for a new career opportunity in New York working for the fashion house of Diane von Furstenberg. Whitney has one old friend, Erin, waiting for her in Manhattan, and a whole host of new people she's getting to know. Although the coast-swapping move is professionally driven, Whitney's excited to for the chance to spend time getting to know Jay, the Australian singer/guitarist she met during an earlier trip east while working for People's Revolution.

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 gets mixed signals from Jay and decides to ask him directly where she stands. 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 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.

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.

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 whole scandal.