After a successful showing, Whitney’s first big sale for her line almost ends in disaster. Erin suspects Olivia of taking undue credit for pulling the perfect look for ELLE’s shoot with pop-singer, Ke$ha
Olivia’s flubs during Fashion Week leave an opening that Erin quickly tries to fill with a new fashion reporter. Roxy impresses Kelly by helping to produce a huge fashion show. Whitney fights for a spot in an emerging designer show in Miami
Whitney doesn’t follow Kelly’s advice and brings Roxy along to a Glamour magazine shoot, and it almost ends in disaster. Erin and Olivia compete to be featured in New York’s biggest gossip column
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
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
Fresh from her breakup with Jay, Whitney questions whether she made the right decision to leave her life in Los Angeles. An opportunity at work may be what Whitney needs, but always competitive Olivia is after the same position
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 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
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
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
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.
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