Life on the Upper East Side is all about power, money, and reputation. This quiz checks how well you know the families, schools, and social rules that define Gossip Girl’s world.
Which borough of New York City do Dan and Jenny Humphrey call home during most of the series?
The Bronx
Manhattan
Brooklyn
Queens
What is the name of the girls’ private school attended by Serena, Blair, and many of their friends?
Constance Prep Academy
Constance Billard School for Girls
Manhattan Elite Ladies School
St. Mary’s Academy for Girls
Where does Nate Archibald’s family expect him to go to college due to legacy pressure?
Columbia
Harvard
Dartmouth
Yale
Which iconic New York City hotel is closely associated with Chuck Bass and his family’s business empire?
The Waldorf Astoria
The Palace Hotel
The Empire Hotel
The Plaza Hotel
What is the name of the fashion company originally run by Blair’s mother Eleanor?
Upper East Style House
Waldorf Designs
Eleanor Atelier
Waldorf Couture
Which character owns an art gallery in Brooklyn and has a history as the lead singer of a band called Lincoln Hawk?
Bart Bass
Rufus Humphrey
Cyrus Rose
William van der Woodsen
Which elegant hotel do the van der Woodsen family and others often use as a residence early in the series?
The Gansevoort Hotel
The Plaza Hotel
The Empire Hotel
The Palace Hotel
Which holiday event in the Hamptons is a recurring setting for summer drama among the Upper East Siders?
Thanksgiving dinners at the Archibalds
Fourth of July parades in Brooklyn
White parties and charity events in the Hamptons
New Year’s Eve parties in Times Square
Which character comes from a powerful political family, with relatives involved in national politics?
Nate Archibald
Dan Humphrey
Eric van der Woodsen
Chuck Bass
Which loyal housekeeper and confidante is practically family to Blair Waldorf and knows many Upper East Side secrets?
Dorota Kishlovsky
Nelly Yuki
Hazel Williams
Isabel Coates
Starter
You picked up some basics about Upper East Side life, but a lot of the finer details escaped you. A rewatch will help you learn how this world really works.
Solid
You understand the key people, places, and expectations that shape Upper East Side life in Gossip Girl. A bit more precision will make your intel nearly flawless.
Expert!
You know the Upper East Side hierarchy, habits, and unwritten rules like a true insider. Your fact-checking skills are as sharp as any Gossip Girl blast.
The Upper East Side in Gossip Girl is practically a character on its own. Understanding its power structures explains a lot about why the characters act the way they do. Gossip Girl Quizzes
