Join or Sign In
Sign in to customize your TV listings
By joining TV Guide, you agree to our Terms of Use and acknowledge the data practices in our Privacy Policy.
The City Season 1 Episodes
Season 1 Episode Guide
23 Episodes 2008 - 2009
Episode 1
If She Can Make It Here...
Mon, Dec 29, 2008 30 mins
In the series opener, Whitney Port arrives in New York City and begins working for iconic fashion designer Diane von Furstenberg.
Episode 2
The Truth Will Reveal Itself
Mon, Dec 29, 2008 30 mins
Whitney doesn't know who to trust when rumors surface that Jay is seeing someone else; Olivia and Whitney meet famed shoe designer Manolo Blahnik.
Episode 3
The L Word
Mon, Jan 5, 2009 30 mins
Erin's new boyfriend visits from Toronto and Whitney decides it's time to find her own place. Later, Jay and Whitney discuss their relationship.
Episode 4
Good Things Come in Threes
Mon, Jan 12, 2009 30 mins
Whitney's receiving mixed signals from Jay, so goes on a date with another guy; Erin's boyfriend Duncan considers moving to New York, but she's not so sure it's a good idea.
Episode 5
Boys Night Out
Mon, Jan 19, 2009 30 mins
Jay's roommate Adam plans a boys' night out, which doesn't sit well with his girlfriend.
Episode 6
He Never Said He Had a Girlfriend
Mon, Jan 26, 2009 30 mins
Jay and Adam host an art-gallery opening, where Allie has a run-in with the girl who claims to have kissed Adam. Meanwhile, there's tension between Jay and Whitney when he takes Adam's side.
Episode 7
The Truth Hurts
Mon, Feb 2, 2009 30 mins
Whitney and Allie attend Kelly Cutrone's birthday party; Erin rekindles the flame with an ex-boyfriend.
Episode 8
Mingling With the Commoners
Mon, Feb 9, 2009 30 mins
Erin's ex-boyfriend admits he still has feelings for her, making her question her relationship with Duncan. Meanwhile, Olivia hooks Jay's band up with a gig, which doesn't go so well.
Episode 9
Unexpected Roommates
Mon, Feb 16, 2009 30 mins
The ladies ring in the New Year; Duncan visits Erin, and the pair have a run in with JR; Adam wants Jay to move out.
Episode 10
The Past Catches Up
Mon, Feb 23, 2009 30 mins
The gang heads to Miami, where Whitney has a run-in with Jay's ex. Meanwhile, there's chemistry between Alli and a male model during a sexy photo shoot.
Episode 11
Fool Me Twice, Shame On Me
Mon, Mar 2, 2009 30 mins
Jay's ex, Danielle, pops up again, making an already wary Whitney rethink her relationship. Meanwhile, Olivia takes credit for Whitney's work at DVF.
Episode 12
I'm Sorry Whit
Mon, Mar 9, 2009 30 mins
Whitney and Jay's relationship hits a roadblock when he waits until the last minute to tell her his band is going on tour.
Episode 13
I Lost Myself in Us
Mon, Mar 16, 2009 30 mins
Whitney's breakup with Jay has her wondering if moving to New York was the right choice after all. Meanwhile, Adam wants Allie to move back in with him.
Episode 14
Sleeping With the Frenemy
Tue, Sep 29, 2009 30 mins
Whitney and Olivia move on from Diane von Furstenberg. Olivia takes a job at Elle magazine, while Whitney goes back to work for Kelly Cutrone. Meanwhile, Whitney's high-school friend, Roxy Olin, arrives in New York looking for a job and a place to crash.
Episode 15
Working Girls
Tue, Oct 6, 2009 30 mins
Roxy steps out of line on her first day working for Kelly Cutrone. Elsewhere, Olivia has a tough time pleasing Erin at Elle.
Episode 16
It's All Who You Know
Tue, Oct 13, 2009 30 mins
Whitney ignores Kelly's advice and shows her designs to Samantha's boss, a buyer for Bergdorf Goodman. Elsewhere, Olivia surprises Erin by succeeding on a tough assignment.
Episode 17
Meet the Fackelmayers
Tue, Oct 20, 2009 30 mins
Whitney decides she's ready to reenter the dating scene and meets a cute younger guy---and his hot older brother. Elsewhere, Olivia thrives at an Elle cocktail party, but Erin's not impressed.
Episode 18
Hit It and Quit It
Tue, Oct 27, 2009 30 mins
Whitney goes on another date with Freddie, who inexplicably brings his father along, and her ex, Jay, is critical of her new beau. Meanwhile, Roxy and Olivia clash when Elle teams up with People's Revolution to throw a party.
Episode 19
Weekend at Freddie's
Tue, Nov 3, 2009 30 mins
Whitney heads to the Hamptons with the girls and learns some surprising news about Freddie. Back in Manhattan, Olivia drops the ball on a big assignment for Elle, forcing Erin to pick up the slack.
Episode 20
Friends and Foe-Workers
Tue, Nov 10, 2009 30 mins
A fight erupts between Whitney and Roxy when the girls attend Miami Fashion Week for work, and Kelly threatens to fire them both. Elsewhere, Olivia fails to complete another assignment at Elle, but this time blame falls on Erin.
Episode 21
Forget About Boys
Tue, Nov 17, 2009 30 mins
Erin grows increasingly frustrated with the preferential treatment Olivia receives at Elle. Meanwhile, Whitney and Roxy go on a series of disastrous dates.
Episode 22
If You Want Something Done Right...
Tue, Nov 24, 2009 30 mins
Whitney takes a big risk when she lets Roxy work on an important project for her fashion line---even though Kelly thinks Roxy can't be trusted. At Elle, Erin and Olivia have a blowup after Olivia comes up short on another assignment.
Episode 23
Everything on the Line
Tue, Dec 1, 2009 30 mins
Erin reaches her breaking point in the Season 1 conclusion and tells Elle boss Joe Zee that he'll have to choose between her and Olivia. Elsewhere, Whitney presents her line to Bergdorf Goodman.
