A whole new life awaits Whitney Port as she packs up her comfortable life in Los Angeles and heads for fashion-forward Manhattan. With an exciting new job at global design house Diane von Furstenberg and a brand new boyfriend, everything seems perfect in Whitney's world... that is until Whitney learns that her "uptown" lifestyle is a complete turn-off to her "downtown" boyfriend, who wants nothing to do with that world.

In the second part of the season premiere, Whitney Port's new romance with rocker Jay hits the skids when an old flame warns her that her new boyfriend may not be deserving of her trust. And while she doubts the purity of his motives, she can't help but wonder if he's telling the truth.

Erin's new boyfriend comes to town and the depth of their relationship makes Whitney question the strength of her own romance with Jay. Also, Whitney searches for a place to live.

Whitney hits it off with Chris, one of Olivia's upper east side friends, sparking jealousy in not-quite-boyfriend Jay.

Jay and Adam's "guys night out" leads to major scandal when Samantha reveals that Adam wasn't exactly faithful to his girlfriend.

The past comes back to haunt Adam when his fling confesses their indiscretion to Allie. Meanwhile, Whitney reaches out to Olivia but is brutally rebuffed.

Kelly Cutrone celebrates her birthday party in Manhattan and her outspoken opinions about Allie's appearance offend the waifish model. Meanwhile, an ex-boyfriend of Erin's comes into town.

Olivia sets up a gig for Tamarama at an upper east side gala, but Jay's hipster attitude clashes with the snobby sophisticates in attendance. Also, Erin reconnects with her first love which could lead to the end of her relationship with Duncan.

Erin's continued flirtation with ex-love J.R. causes turmoil in her relationship with Duncan, who refuses to play a part in her love triangle. Meanwhile, Adam kicks Jay out of their apartment which leads Whitney to consider the obvious: is it to soon for Jay to move in with her? Also, Olivia tires of Nevan's continual mooching.

Temptation is the name of the game this week as the gang heads to Miami for some New Year's fun in the sun. Allie feels heat with a colleague during an intense modeling shoot, sending boyfriend Adam into fits of jealousy. Meanwhile, Whitney worries when Jay's old flame warns her that he may not be being honest with her.

Alixe Boyer offers Whitney and Olivia a fantastic opportunity: the chance to dress a celebrity for the cover of Elle magazine. But Olivia proves just how vicious she can be when she steals the credit for Whitney's work. Meanwhile, Whitney's distrust of Jay continues to deepen, especially since a certain blonde ex-girlfriend of his is back in the city...

Whitney is hurt to learn that Jay is leaving on tour and didn't bother to tell her. Can their romance survive this final test? Meanwhile, an assignment at Diane von Furstenberg promises to separate the fashion frauds from the fashion-forward.

Whitney wonders if moving to New York was a mistake after her breakup with Jay. Meanwhile, Adam wishes for Allie to move in with him once again.

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Erin has to pick up the slack when Olivia drops the ball on a big interview assignment for ELLE. Plus, Whitney finds out a shady secret about Freddie from his own brother.

Roxy and Whitney get into an argument while on the job at Miami Fashion Week

Olivia gets praise from Joe at an ELLE photo shoot, but Erin is frustrated about the preferential treatment. Meanwhile, Whitney and Roxy go on a series of disastrous dates, ending in a blowup at a night club.

At People's Revolution, Whitney gives Kelly the first look at her design samples. Kelly evaluates the rack of clothes and tells Whitney her next step is to make a look book for her pieces.

At People's Revolution, Kelly tells Whitney that she sent her look book to Bergdorf Goodman, and Linda Fargo, the senior vice president at Bergdorf, liked what she saw.