From Blair Waldorf's Headband to Chuck Bass's Smirk: The Ultimate Gossip Girl Obsession Quiz

This trivia quiz will test your knowledge of the iconic TV series "Gossip Girl," covering characters, plot twists, and memorable moments. Ready to prove you're a true Upper East Sider? Let’s get started!

Welcome to the Ultimate Gossip Girl Obsession Quiz!

This trivia quiz will test your knowledge of the iconic TV series "Gossip Girl," covering characters, plot twists, and memorable moments. Each question is designed to challenge your expertise on all things Gossip Girl.

Ready to prove you're a true Upper East Sider? Let’s get started!

🗽 Who is revealed to be the original Gossip Girl?
Dan HumphreySerena van der WoodsenNate ArchibaldBlair Waldorf
🗽 In the first episode, Serena's unexpected return to Manhattan becomes the center of attention. Where was she?
Rehab in FloridaBoarding school in FloridaTraveling around EuropeBoarding school in Connecticut
🗽 Which prestigious school do the main characters attend?
Bayside HighWest Beverly HighChilton AcademyConstance Billard School for Girls and St. Jude's School for Boys
🗽 Who is Chuck Bass’s father?
JackWilliamRufus Bart
🗽 Jenny Humphrey has mad calligraphy skills. For what party is she writing the invitations?
The SpeakeasyMasquerade BallKiss on the LipsDebutante Ball
🗽 What is the name of Blair Waldorf’s maid?
Penelope Dorota Hazel Vanya
🗽 Who does Nate Archibald have an affair with in season 1?
Jenny SerenaBlair’s mother, Eleanor WaldorfVanessa
🗽 Where do Blair and Chuck make out for the first time??
In a limousineIn a clubAt schoolAt Chuck's hotel
🗽 What is the name of Dan Humphrey’s first book?
ExposedInsideRevealedOutside
🗽 What is the signature drink of Chuck Bass?
ScotchOld FashionedManhattanMartini
🗽 Who is Lily’s first husband?
RufusKeithBart William
🗽 There's a dish Rufus cooks every morning. What is it?
WafflesEnglish breakfastEggsPancakes
🗽 Hilary Duff starred in Gossip Girl and had a short affair with Dan. What character did she portray?
MarciaOlivia LivRachel
🗽 Who did Blair Waldorf marry first?
Nate ArchibaldPrince Louis GrimaldiDan HumphreyChuck Bass
🗽 Which character has a sister named Jenny?
Chuck Dan Rufus Nate
🗽 Which Ivy League university does Blair dream of attending?
Princeton UniversityColumbia UniversityHarvard UniversityYale University
🗽 Two of two of Lily van der Woodsen’s love interests have almost identical names. Name them
Jayden and JaidenKlaus and ClausAiden and AdenJeffrey and Geoffrey
🗽 At graduation, Gossip Girl sends a crushing e-mail humiliating the majority of the senior class. What does she call Serena?
LiarInvisibleBoringIrrelevant
🗽 Who voices Gossip Girl?
Kristin DavisMila KunisKristin BauerKristen Bell
🗽 What character becomes Blair's roommate at NYU?
JulietPoppySerenaGeorgina

More Like This
Are You More Julien or Zoya? Take This Definitive New "Gossip Girl" Personality Test to Reveal Your True Character
Are You More Julien or Zoya? Take This Definitive New "Gossip Girl" Personality Test to Reveal Your True Character quiz
Would You Rather: Blair Waldorf’s Most Iconic Decisions in 'Gossip Girl'
Would You Rather: Blair Waldorf’s Most Iconic Decisions in 'Gossip Girl' quiz
Would You Rather: Serena van der Woodsen’s Most Daring Choices in 'Gossip Girl'
Would You Rather: Serena van der Woodsen’s Most Daring Choices in 'Gossip Girl' quiz
'Gossip Girl' Word Quest: Can You Guess the Upper East Side Parents by First and Last Letter?
'Gossip Girl' Word Quest: Can You Guess the Upper East Side Parents by First and Last Letter? word quest
Find Out Which 'Gossip Girl' Icon You Embody!
Find Out Which 'Gossip Girl' Icon You Embody! quiz
What's Your Gossip Girl Alter Ego?
What's Your Gossip Girl Alter Ego? quiz
Can You Name the Gossip Girl Characters?
Can You Name the Gossip Girl Characters? word quest
Gossip Girl Stars Quiz: Test Your Upper East Side Knowledge!
Gossip Girl Stars Quiz: Test Your Upper East Side Knowledge! trivia quiz
Gossip Girl: XOXO, A Trivia Challenge! (VIDEO QUIZ)
Gossip Girl: XOXO, A Trivia Challenge! (VIDEO QUIZ) video
Character Conundrum: Iconic TV Personalities Quiz
Character Conundrum: Iconic TV Personalities Quiz trivia quiz
Beyond XOXO: Dive Deep into Gossip Girl Trivia! (VIDEO QUIZ)
Beyond XOXO: Dive Deep into Gossip Girl Trivia! (VIDEO QUIZ) video
Upper East Side Entanglements: Gossip Girl Love Lives Quiz! (VIDEO QUIZ)
Upper East Side Entanglements: Gossip Girl Love Lives Quiz! (VIDEO QUIZ) video
XOXO, Who Said That? Guess the Gossip Girl Character! (VIDEO QUIZ)
XOXO, Who Said That? Guess the Gossip Girl Character! (VIDEO QUIZ) video
XOXO, Do You Know Your Gossip Girl? Test Your Upper East Side Savvy! (VIDEO QUIZ)
XOXO, Do You Know Your Gossip Girl? Test Your Upper East Side Savvy! (VIDEO QUIZ) video
XOXO: Match the Quote to the Gossip Girl Character! (VIDEO QUIZ)
XOXO: Match the Quote to the Gossip Girl Character! (VIDEO QUIZ) video
Who's Your Perfect Gossip Girl Partner in Crime?
Who's Your Perfect Gossip Girl Partner in Crime? quiz
Upper East Side Elite or Brooklyn Dreamer? Your Gossip Girl World Quiz
Upper East Side Elite or Brooklyn Dreamer? Your Gossip Girl World Quiz quiz
Can You Keep a Secret? The Ultimate Gossip Girl Betrayal Quiz!
Can You Keep a Secret? The Ultimate Gossip Girl Betrayal Quiz! quiz
Which Gossip Girl Character Are You?
Which Gossip Girl Character Are You? quiz
XOXO, Which Gossip Girl Character Are You?
XOXO, Which Gossip Girl Character Are You? quiz
Gossip Girl Quiz: Who Are You on the Upper East Side?
Gossip Girl Quiz: Who Are You on the Upper East Side? quiz
Headbands or Headbands Not? Your Ultimate Gossip Girl Style Quiz
Headbands or Headbands Not? Your Ultimate Gossip Girl Style Quiz quiz
Blasting Secrets or Keeping Quiet? A Gossip Girl Morality Quiz
Blasting Secrets or Keeping Quiet? A Gossip Girl Morality Quiz quiz
Gossip Girl Spilled One of Your Secrets. What Is It?
Gossip Girl Spilled One of Your Secrets. What Is It? quiz
XOXO: Test Your Gossip Girl Knowledge with This Fun Quiz
XOXO: Test Your Gossip Girl Knowledge with This Fun Quiz trivia quiz
Gossip Girl Love Lives Quiz: Who Dated Who?
Gossip Girl Love Lives Quiz: Who Dated Who? trivia quiz
Guess the Gossip Girl Character: Can You Name Them All?
Guess the Gossip Girl Character: Can You Name Them All? trivia quiz
Ultimate Gossip Girl Trivia: How Well Do You Know the Upper East Side?
Ultimate Gossip Girl Trivia: How Well Do You Know the Upper East Side? trivia quiz
Blair or Serena? Which Gossip Girl Icon Are You?
Blair or Serena? Which Gossip Girl Icon Are You? quiz
XOXO, Who Said That? Test Your Gossip Girl Quote Knowledge
XOXO, Who Said That? Test Your Gossip Girl Quote Knowledge trivia quiz
Which 'Gossip Girl" Character is the Perfect Girlfriend for You?
Which 'Gossip Girl" Character is the Perfect Girlfriend for You? quiz
Which "Gossip Girl" Male Character is the Perfect Match for You?
Which "Gossip Girl" Male Character is the Perfect Match for You? quiz
Which 'Gossip Girl' Character Would You Be Best Friends With?
Which 'Gossip Girl' Character Would You Be Best Friends With? quiz
Latest
Winter Holiday Activities First and Last Letter Word Quest
Winter Holiday Activities First and Last Letter Word Quest word quest
Christmas Urban Legends That Still Freak People Out
Christmas Urban Legends That Still Freak People Out article
Would You Rather: Make These Impossible Choices from Your Favorite Rom-Coms
Would You Rather: Make These Impossible Choices from Your Favorite Rom-Coms quiz
Relationship Compatibility Quiz: Are You Meant to Be?
Relationship Compatibility Quiz: Are You Meant to Be? quiz
Your 2025 Year in Review: What Defined You This Year?
Your 2025 Year in Review: What Defined You This Year? quiz
Zodiac Compatibility Quiz: Who's Your Perfect Match?
Zodiac Compatibility Quiz: Who's Your Perfect Match? quiz
What Will Your 2026 Look Like? Personality Quiz
What Will Your 2026 Look Like? Personality Quiz quiz
Career Change Quiz: What Should You Do in 2026?
Career Change Quiz: What Should You Do in 2026? quiz
What's Your Love Language? Relationship Quiz
What's Your Love Language? Relationship Quiz quiz
See all