Dan Humphrey starts as an outsider with a notebook and ends as the mind behind Gossip Girl. This quiz traces his evolution from Brooklyn boy to anonymous narrator.
Where does Dan Humphrey live with his family for most of the series?
Queens
New Jersey suburbs
Brooklyn
Upper East Side
What nickname does Gossip Girl often use for Dan early in the series?
Scholarship Kid
Brooklyn Boy
Lonely Boy
Outsider Dan
Which school does Dan attend on scholarship at the beginning of the series?
Constance Billard School for Boys
Columbia Prep
Brooklyn Academy High
St. Jude’s School for Boys
What is Dan’s primary career ambition throughout most of the series?
To be a successful writer
To become a lawyer
To be a fashion designer
To run a hotel like Chuck
Which famous magazine does Dan eventually work with, helping to launch his writing career?
Vanity Fair is referenced in connection with his writing career
Vogue hires him as a full-time editor
Time names him editor in chief at a young age
Rolling Stone makes him a music critic
What is the title of Dan’s roman a clef novel loosely based on his friends and Upper East Side life?
Lonely Boy’s Journal
Uptown Stories
Inside
Gossip and the City
Which major reveal about Dan is made in the series finale of Gossip Girl?
He secretly funded Nate’s newspaper alone
He is actually related to Chuck Bass
He was Gossip Girl all along
He had been sending fake tips to Gossip Girl only
How does Dan say that Gossip Girl helped him become part of the Upper East Side world?
By providing him with anonymous money and power
By giving him a way to observe, write about, and influence that world
By letting him blackmail teachers for better grades
By making him a secret partner in Bass Industries
Which friendship from his childhood provides Dan with a point of comparison between Brooklyn and the Upper East Side?
His friendship with Trip van der Bilt
His friendship with Carter Baizen
His friendship with Vanessa Abrams
His friendship with Nate Archibald
By the end of the series, whom does Dan marry, closing the loop on his romantic story?
Jenny Humphrey’s friend to be closer to family
Serena van der Woodsen
Vanessa Abrams
Blair Waldorf
Starter
You remembered Dan as Lonely Boy, but many details about his choices and writing were unclear. Following his career and secrets more closely will reveal how he changed.
Solid
You understand Dan’s relationships, ambitions, and eventual reveal as Gossip Girl. A bit more focus on how he used his writing will complete your picture of him.
Expert!
You know Dan Humphrey’s journey from wannabe insider to the ultimate observer in impressive detail. Your insight into his motives goes right to the heart of the series.
Dan’s story shows how powerful storytelling and ambition can be, for better or worse. Knowing exactly how he built Gossip Girl explains many of the show’s wildest twists. Gossip Girl Quizzes
