Episode PremiereDecember 29, 2008
Show Period2008 - 2010
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. Erin and Jay, along with his roommate Adam, round out her "downtown" circle of friends; Olivia, a self-described "social," is a new colleague at DvF and invites Whitney into her "uptown" world.
Arriving at the Diane von Furstenberg offices in Manhattan's Meatpacking District, Whitney is ready for her first day on the job. She's given a quick tour of the office and meets Olivia for the first time. Olivia is quick to grill her about who she knows in New York, as well as about her budding romance with Jay. Olivia also tells Whitney about a dinner party she's planning to throw at her apartment, but it's just small talk so far, and she doesn't offer an invitation.
Back at her temporary home in Erin's apartment in the city's Gramercy section, Whitney gives Erin the scoop on her first day at DvF and her experience meeting Olivia. When Erin mentions that she knows Olivia, the city suddenly begins to seem like a pretty small world. The conversation then segues into Whitney's date with Jay that evening.
Whitney arrives at Nero to find Jay waiting for her on the patio. They toast her first day at DvF and Jay offers to be Whitney's personal tour guide of the city. They flirt, giggle and touch ... and it isn't long before they're calling for the check.
The next morning, Whitney recaps her date for Erin. She admits to going to Jay's place after Nero and to "really, really" liking him. Surprisingly not tired after her first day and big night out, Whitney tells Erin that she's looking forward to her second day on the job.
Cut to the DvF show at New York City's Fashion Week: Celebrities Rosario Dawson, Eva Longoria Parker, Jennifer Lopez and Molly Sims are all spotted in the audience. Whitney finds her skills put to the test quickly as she works the back of the house, while Olivia does her job out front. The show goes off without a hitch and the DvF team head to 60 Thompson for the after party. During the soiree, Whitney and Olivia have a brief encounter with Samantha, an assistant buyer at retailer Bergdorf Goodman, after which Olivia makes a comment about the quality of her handshake.
Alixe Boyer, VP, Global Image Director at Diane von Furstenberg, tells Whitney that they've received great feedback on the show, including how smoothly things ran in the back of the house. It's a great start for Whitney! Olivia observes the conversation between the two and later asks Whitney about it. After the recap, Olivia opens up and invites Whitney to her dinner party, and asks her to bring Jay along, too.
When Whitney next meets up with Jay for lunch, she fills him in on Olivia and the dinner party invitation. Like Erin, Jay is also familiar with Olivia and in his opinion, doesn't find her to be very genuine. He also tells Whitney that he's not too keen on the socialite scene. Whitney asks him if he'll accompany her to Olivia's dinner party, even just for the sake of hanging out with her. Jay declines and tells Whitney that he tends to do only what he wants to do.
In Erin's bathroom, while getting ready for Olivia's party. Erin wonders if it will be OK that she's going with Whitney instead of Jay. Whitney assures her it will be fine.
Olivia is putting the final touches on her table setting as the guests begin to arrive. When Whitney and Erin make their entrance, introductions are made all around. When Olivia asks Whitney about Jay's whereabouts, she tells her simply that he wasn't able to make it. As the group sits down to dinner, a toast is made in honor of Olivia, and Olivia, in turn, toasts Whitney, welcoming her to New York. During dinner, Olivia halts the conversation to inquire again about Jay. She wants to know why he wasn't able to attend. Whitney, seemingly caught in an awkward position, says that she's not sure why Jay didn't make it to the party. Olivia then asks Whitney if they're the kind of couple that miss each other when they're not together. Even more uncomfortable, Whitney manages to say that she can't speak for how Jay feels, but as for herself, yes, she thinks about Jay when she's not with him.
Meanwhile, Jay has been shooting pool with his roommate Adam. Jay mentions that he's glad to be having a guys' night again as he's recently been spending most of his time with Whitney. Jay confesses that he feels things are going really fast between them and that he hasn't had a chance to get his head around it. He also tells Adam that he skipped out on attending Olivia's dinner party. Adam backs him up and agrees that taking things at your own pace is the best way to go.
Back at Olivia's, the dinner party continues and Erin and Whitney are chatting with all the guests. Suddenly a new guest enters the scene. Whitney breaks into a huge grin as she spots Jay, champagne bottle in hand.
After greeting the rest of the guests, Jay and Whitney share a few quiet moments together apart from the group. When he asks her if she wants to leave the party, she's on board. Whitney grabs Erin and the three of them say their goodbyes, much to the surprise of the other dinner guests.