Whitney struggles between furthering her business and her loyalties to Kelly. Meanwhile, Olivia's trip to Japan is a big hit with ELLE, much to Erin's chagrin.

Tensions rise between Roxy and Whitney and it forces Roxy to search for a new home.

Tonight on the After Show we discuss Whitney and Roxy's fight, we recap your best Twitter comments and check out Jessi's prom date!!

Roxy and Whitney's relationship is put to the test over a failed styling job. Olivia helps Erin pull looks for an ELLE segment on 'The Martha Stewart Show.'

Tonight on the After Show we discuss Kelly's very important assignment, Roxy and Whitney's fight and we have a sneak peak of Jessi's prom!

Whitney pushes her line to fashion trade show buyers and blames Roxy for a failed sale. Plus, Olivia pulls a winning look for the Ke$ha shoot, but Erin suspects foul play.

Tonight on the After Show we discuss Olivia's kryptonite, we update Jessi's prom status and Dan and Jessi try to win you prizes in the After Show Face-off!

Roxy and Whitney put on a runway show in Miami for Whitney Eve without Kelly's help. Olivia promises to come through at work on a big interview.

Tonight on the After Show we show topless photos of Taylor Lautner and Kelly Cutrone takes Dan and Jessi clothes shopping!

Olivia's job is in jeopardy, Roxy impresses Kelly at work, and Whitney pursues new business opportunities.

Tonight on the After Show, Kelly Cutrone stops by for a surprise visit and gives her take on the hottest stories in pop culture!

Roxy ignores Kelly's instructions when she pitches Whitney's collection at an event for another designer. Plus, Olivia ignores a work request of her own.

Olivia party hops with Joe while Erin gossips about her with a reporter. Plus, Whitney's reputation is threatened by Roxy's bad judgement.

Tonight on the After Show we discuss Olivia's butt kissing, 50 Cent's new look and we pull a Kelly Cutrone and scare our new interns!

Erin and Olivia bump heads on how to dress Fergie for an ELLE cover shoot. Meanwhile, Whitney is torn when a French photographer wants to take the relationship to the next level.

Tonight on the After Show we discuss Whitney getting personal with Kelly and who has Justin Bieber been kissing?

Tonight on the After Show we discuss Whitney's cute war photographer, Justin Bieber on Oprah and we debut a new game called the After Show Face-off.

Olivia faces backlash after blowing off her interview with Whitney for ELLE.com. Meanwhile, Roxy has a meeting with Zach that seems a lot more like a date.

Tonight on The After Show we discuss Roxy's hunky new photographer, Jessi talks boys with Adam Lambert and Halle Berry is verbally abusive.

Roxy branches out to help direct a photo shoot with a cute, edgy photographer, and Olivia refuses to support Whitney's line at ELLE Magazine.

Whitney Port joins The After Show to discuss the season premier of 'The City' and her famous new boyfriend.

Whitney scrambles to pull her collection together in time for her show at New York Fashion Week, and Olivia shines in her new role at ELLE.com.

THE CITY SEASON 2 PREMIERES APRIL 28TH AT 10:00 PM ET ON MTV

We talk to the cast of The Hills and The City in NYC to get the inside scoop of what happened on both finales.

The 'Hills' and 'City' casts answer burning questions and reveal juicy behind-the-scenes secrets.

Whitney is given a great opportunity but is advised to leave Roxy out of it and Erin and Olivia's conflicting ways cause an on-air disaster.

Olviia and Erin continue to hate each other, Roxy books some angry models and there's a cake fight. Plus we have the Taylor Lautner showdown.

Erin and Olivia get into their biggest fight yet when Olivia comes up short on a new assignment, and Roxy makes a mess of things at Whitney's look book photo shoot.

Whitney and Roxy go on a series of disastrous dates, ending in a blowup at a night club and Erin becomes jealous of Olivia.

Cobra Starship dish on Erin and Olivia, we talk about Whitney's terrible blind date and Dan lives up to his contract and appears topless.

After Show Alice talks about appearing in the Mara Hoffman show and Dan interns for FASHION magazine.

Roxy and Whitney get into an argument while on the job at Miami Fashion Week, and Kelly wonders if the girls should work together.

We talk about The City cast's appearance on Oprah, Freddie calls into the show (after we say some not nice things about him) and Dan meets Alexa Chung.

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.

Today on The Aftershow, Jessi conducts an interview with Taylor Lautner and we have Whitney on the line from New York.

Whitney and Freddie's date sprouts a third wheel when he brings his dad along and Roxy learns firsthand what it's like to work with.

Today on The Aftershow, we talk about Olivia stealing the show from Erin while Whitney and Sammy go shopping for shoes.

Olivia thrives at an ELLE party, but Erin reminds her that the fashion business isn't just about who you know. Whitney reenters the dating scene when she meets a cute new guy.

The cast of Peak Season join us today to talk about the all the drama in the latest episode of The City.

Olivia shocks Erin by succeeding at her biggest assignment yet for ELLE and Whitney goes behind Kelly Cutrone's back when she shows her designs to Bergdorf Goodman.

Today on The Aftershow, Roxy calls to give us an inside scoop on the dirt behind the show that you don't see.

Whitney questions if working with her friend is a good idea when Roxy steps out of line on her first day on the job.

The City is back and we're here to dissect every bit of drama surrounding Whitney in the latest episode.

Whitney's old high school friend Roxy moves in and throws a wild party, and Olivia starts a new job and new drama at Elle Magazine.

A NEW SEASON OF THE CITY PREMIERES SEPTEMBER 30TH AT 10:00 PM ET ON MTV

Whitney questions her life in New York City as she struggles with her break-up and competes with Olivia for new responsibilities at DVF.

In the season finale of 'The City' After Show, Whitney calls in live to give us the scoop on walking away from Jay, plus find out whether she'll be making an appearance on 'The Hills.'

Whitney and Olivia give a presentation for DVF's new handbag collection. Jay's band is going on tour and Whitney and Jay are about to find out if their relationship can take it.

Adam calls into the show and chats about the alleged cheating incident, plus 'The District' star Barack Obama calls into the show!

Whitney is crushed when she discovers that Jay's mysterious night out was spent with his ex-girlfriend. Olivia steals the credit from Whitney when they style an ELLE cover shoot and Allie moves in with Erin.

Olivia shares her side of the story and puts to rest some misconceptions, plus get the scoop on her birthday weekend!

Jay runs into an ex-girlfriend while in Miami 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 and Erin drop in and dish about the cast. Plus, Jessi and Dan reveal an exclusive clip from the show that could change the show completely!

It's New Years Eve on The City and the gang plan to celebrate with drama as jealousy threatens to rip Erin and Duncan apart and Jay struggles with his living arrangements.

Dan and Jessi decode Olivia speak and discuss their favorite moments from 'The City' plus much more.

Jay tells us what he really thinks about Nevan's heckling plus find whether he's used the L-word and much more.

Olivia invites Jay's band to perform at a charity event but her plan backfires, leaving Whitney and Olivia at odds. Meanwhile, Erin's new relationship is threatened by her renewed feelings for her ex-boyfriend.

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.

From the confrontation with Allie to her thoughts on Adam, Kelly Cutrone gives it to us straight on The After Show.

Allie calls into The After Show to give Dan and Jessi the backstory on her relationship with Adam, plus take a look at Allie's Diesel ad and more!

Allie breaks down after a run in with the girl who claims she kissed Adam. Whitney gets upset with Jay for taking Adam's side.

Season 1 of The City has featured music videos by some of today's hottest artists. Check out some of their videos including videos by Estelle, TV On the Radio, Beyonce, and more.

Erin calls into The After Show to give Dan and Jessi the backstory on her relationship with Whitney, plus the scoop on the alleged kiss and more!

Adam finds himself in hot water with Allie when she hears that he kissed another girl. Olivia reluctantly agrees to let Nevan crash on her couch.

Whitney's date with a new guy makes Jay jealous and leads him confess his true feelings. Erin thinks things are moving too fast with Duncan when he suggests moving in.

Whitney calls in to give Jessi and Dan the scoop on her (now official) boyfriend, Olivia and more. Plus, get a sneak peek of Jay's music video debut.

When Erin's new boyfriend comes to visit, Whitney decides it's time to find her own apartment as she receives mixed signals from Jay and decides to ask him directly where she stands.

Whitney starts her new job with Diane Von Furstenberg. Her first week promises to be a busy one considering it's fashion week, but she still makes time to go on a date with Jay and to go to Olivia's dinner party.

When Alex resurfaces in Whitney's life he brings a whole lot of drama with him. After Alex and Jay almost get into a fight at a club Whitney is left not knowing who to trust.

Take a look back with Whitney as she reminisces about her adventures in LA to her new life in New York City.

Take a sneak peek at Whitney's upcoming show 'The City' before it premieres December 29th on MTV.