The City

From The Hills to The City is hosted by Whitney Port as she looks back on her life in Los Angeles before making her move to the fashion capital of the world, New York City.

Whitney arrives in New York City during fashion week just in time to start her new career with iconic designer, Diane Von Furstenberg. But when she's invited to an "uptown" dinner party by her new coworker Olivia Palermo Whitney discovers her "downtown" boyfriend wants no part of that world.

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.

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. Allie gets Erin a job at her modeling agency.

Olivia invites Jay's band to perform at one her charity events but her plan backfires.

Adam kicks Jay out of his apartment so Allie can move in permanently and Jay asks Whitney if he can live with her. Erin's plan to juggle two guys backfires when Duncan and J.R. meet face-to-face, leaving her all alone on New Year's Eve. Olivia is fed up with Nevan crashing on her couch and tells him it's time to find his own place.

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. Allie considers breaking up with Adam after she goes on a date with a model she meets at a photo shoot.

Whitney is crushed when she 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 and moves in with Erin.

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. Whitney has to pick up the slack when Olivia is unprepared for a big meeting at work.

During NY Fashion Week, Whitney and Olivia compete for new responsibilities, and Whitney confronts Olivia about the Elle cover pull. Adam confronts Erin when she meddles in his relationship with Allie. Allie considers giving Adam another chance. Whitney gets advice from Diane von Furstenberg about her relationship with Jay ending with a moment no one saw coming... not even Whitney.

Olivia takes a job at ELLE Magazine, but meets her match in co-worker Erin Kaplan. Whitney goes back to work for Kelly Cutrone, and an old friend Roxy comes to town, looking for a job and a place to crash.

Whitney questions if working with her friend is a good idea when Roxy steps out of line on her first day on the job. Olivia wins Joe Zee?s approval on a new project at ELLE, but Erin is tougher to please.

Whitney takes Roxy?s advice and goes behind Kelly's back to show her fashion designs to Bergdorf Goodman. Olivia shocks Erin by calling on her connections in the fashion world and succeeding at her biggest assignment yet.

Whitney reenters the dating scene and meets a cute younger guy, and his hot older brother. When Olivia thrives at an ELLE Magazine cocktail party, Erin quickly reminds her that the fashion business isn?t just about who ya know.

Whitney grows cautious about Freddie just as her ex-boyfriend Jay comes back into the picture. Roxy clashes with Olivia when People?s Revolution and Elle join forces to put on a party.

On a weekend trip to the Hamptons with the girls, Whitney finds out some surprising news about Freddie. Erin has to pick up the slack when Olivia drops the ball on a big interview assignment for ELLE.

When Whitney fights with Roxy at Miami Fashion Week, Kelly questions whether or not the girls should work together at all. Erin expects Joe Zee to come down hard on Olivia for failing a task, but it's Erin who gets in trouble .

Whitney and Roxy go on a series of disastrous dates, ending in a blowup at a night club. When Olivia gets preferential treatment on an ELLE photo shoot, Erin reveals the real reasons she has issues with Olivia.

Whitney gambles by letting Roxy work a big project for her fashion line, even though Kelly thinks Roxy can?t be trusted. When Olivia comes up short on a new assignment, Erin and Olivia get into their biggest fight yet.

A sales presentation with Bergdorf Goodman doesn't go quite as Whitney planned, but it leads to an even bigger opportunity for Whitney and her fledgling fashion line. Erin's frustrations with Olivia reach new heights.