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The Business of the Upper East Side: Gossip Girl Career Quiz

Behind every ball and brunch, there are boardrooms, brands, and big deals. Test your knowledge of the careers and businesses that power Gossip Girl.

What is the name of Chuck Bass’s family company that he fights to control?

Empire Enterprises

Bass Industries

Van der Woodsen Holdings

Humphrey Media Group

Chuck’s main corporate battleground is Bass Industries, his late father’s conglomerate.

Eleanor Waldorf owns a company in which industry?

Investment banking

Fashion design

Restaurant chains

Hotel management

Eleanor’s company focuses on fashion design, with Blair often involved in Waldorf Designs.

What is the name of the media outlet that Nate Archibald eventually runs?

The Manhattan Times

The Spectator

The New Yorker

The Upper East Gazette

Nate becomes editor in chief and later owner of The Spectator, a media outlet he tries to make more ethical.

Dan Humphrey’s book about the Upper East Side is titled what?

Uptown Stories

The Upper East Siders

Inside

Gossip and Glamour

Dan publishes Inside, a fictionalized account of his friends and the elite world they inhabit.

What is Rufus Humphrey’s primary business venture for much of the series?

Running a law firm

Owning an art gallery

Managing a hedge fund

Owning a restaurant chain

Rufus transitions from rock musician to art gallery owner, representing artists in Brooklyn.

Which character becomes heavily involved with Waldorf Designs after Blair takes over?

Georgina Sparks

Blair Waldorf

Jenny Humphrey

Serena van der Woodsen

Blair eventually steps into a leadership role at Waldorf Designs, shaping its image and direction.

What type of business does Bart Bass primarily operate through Bass Industries?

Real estate and hotels

Food and beverage franchises

Sports teams and stadiums

Tech startups and apps

Bart Bass made his fortune in real estate and hotels, setting up Chuck’s future with the Empire Hotel.

Which character briefly runs a public relations firm that Serena works for?

K.C. Cunningham

Maureen van der Bilt

CeCe Rhodes

Lola Rhodes

Serena works with K.C. Cunningham at a public relations firm focused on high profile clients.

Which character builds a career in politics connected to the van der Bilt family?

Ben Donovan

Damien Dalgaard

Tripp van der Bilt

Carter Baizen

Tripp van der Bilt is Nate’s cousin and a politician whose career becomes entangled with Serena.

By the time of the flash-forward, Nate is shown considering a run for which office?

Governor of New York

President of the United States

Mayor of New York City

United States Senator

In the finale flash-forward, Nate’s success with The Spectator has him being talked about as a potential mayoral candidate.

Starter

You remember some of the jobs and companies, but a few Upper East Side business details slipped by.

Solid

Nice work. You clearly tracked many of the careers and corporate shake ups in the series.

Expert!

You could probably pitch a new deal at Bass Industries or Waldorf Designs and fit right in.

From fashion houses to media empires, Gossip Girl shows how business and ambition shape life on the Upper East Side as much as romance does. Gossip Girl Trivia Quizzes

Hi, I’m Aniruddh Sharma – the creator of Quiz Crest. I started QuizCrest with a simple idea: learning about Bollywood, Hollywood, cricket, music, history, and more doesn’t have to be boring or overwhelming. With so much trivia, facts, and stories out…

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