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50 free You've Got Mail trivia questions with answers — entertainment quiz, new questions added Aug 2026.
Don't you love New York in the fall? This You've Got Mail trivia quiz has 50 free questions with answers about Nora Ephron's 1998 romantic comedy: Kathleen Kelly and her children's bookstore, Joe Fox and the chain that swallows it, the AOL screen names, the dog at the end, and the Upper West Side locations where the third Hanks-Ryan pairing was filmed. The early questions are easy for anyone who has seen the movie once. Later ones cover the 1937 Hungarian play and the 1940 Lubitsch film that started it all, the supporting cast from Greg Kinnear to Dave Chappelle, casting stories, the Harry Nilsson-heavy soundtrack, budgets and grosses, and the Ephron sisters' careers, so even devoted fans should find a few surprises. Play it on movie night, in a book-club round or to settle who really remembers the film. Every answer was checked against Wikipedia's articles on the film, its sources and its cast, and each question links to the page and sentence that supports it.
30 of 50 questions with answers and explanations. Play the quiz
Q 01Who directed You've Got Mail?
Nora Ephron
It became her highest-grossing film and opened at number one in North America.
Q 02The film was the third pairing of Tom Hanks and Meg Ryan. Which was their first?
Joe Versus the Volcano
Their second, Sleepless in Seattle, was also directed by Ephron.
Q 03The film's title comes from what?
The AOL greeting for a new email
Kathleen and Joe correspond on AOL accounts, she on a laptop while her boyfriend clings to his typewriter.
Q 04The plot is drawn from a 1937 Hungarian play. What is it called?
Parfumerie
Miklós László's play had already been filmed twice before Ephron got to it.
Q 05Which 1940 Ernst Lubitsch film is the direct ancestor of You've Got Mail?
The Shop Around the Corner
James Stewart and Margaret Sullavan play feuding Budapest shop clerks who are secretly pen pals.
Q 06The 1949 musical version, In the Good Old Summertime, moved the story to which city?
Chicago
Judy Garland and Van Johnson work in a turn-of-the-century music store instead of a Budapest leather shop.
Q 07Which 1963 Broadway musical is also based on the same Hungarian play?
She Loves Me
Jerry Bock and Sheldon Harnick wrote it; its 2016 revival was the first Broadway show ever live-streamed.
Q 08What is the name of Kathleen Kelly's bookstore?
The Shop Around the Corner
The name is a nod to the 1940 film. She inherited the shop from her mother.
Q 09What is the specialty of Kathleen's shop?
Children's books
Delia Ephron said the sisters chose it because they grew up loving children's books more than anything.
Q 10What is Kathleen's AOL screen name?
Shopgirl
She met her correspondent in a chatroom and they agreed not to share personal specifics.
Q 11What is Joe Fox's screen name?
NY152
His family runs the chain that is opening a few blocks from Kathleen's shop.
Q 12What is the name of the bookstore chain owned by Joe's family?
Fox Books
He is overseeing the new storefront's opening while dating the abrasive Patricia Eden.
Q 13Kathleen's boyfriend Frank Navasky writes a column for which newspaper?
The New York Observer
He is a left-leaning columnist devoted to his typewriter; Greg Kinnear plays him.
Q 14What are the names of Kathleen's three shop assistants?
Q 21Which Monty Python member's role as a Thomas Pynchon-like novelist was cut from the film?
Michael Palin
His scenes never made the final edit.
Q 22Ephron had Meg Ryan and Heather Burns spend a week working where before filming?
Books of Wonder, a real children's bookstore
The idea was to get them into character as bookshop staff who cared about the history of children's literature.
Q 23Where was most of the film shot, between February and June 1998?
Manhattan's Upper West Side
George, Birdie and Christina
They worry the new chain store will hurt business, and Kathleen brushes them off.
Q 15When Joe first visits Kathleen's shop for storytime, whom is he taking out?
His 11-year-old aunt and 4-year-old half-brother
The joke of a grown man having a little-girl aunt was borrowed from an 1891 Israel Zangwill story.
Q 16Which of Joe's employees peeks through the café window and tells him that his pen pal is Kathleen?
Kevin
Joe's store manager and confidant is played by a stand-up comedian.
Q 17After closing her shop, what does Kathleen decide to do?
Write children's books
Business declined steadily while the chain store thrived, despite picketing and talk-show appearances on her behalf.
Q 18What is the name of Joe's dog, whose name Kathleen hears called at the final meeting?
Brinkley
Hearing the dog's name is how she realizes who her pen pal is, and she admits she had hoped it would be him.
Q 19Which Jane Austen novel do Joe and Kathleen discuss, mirroring their own relationship?
Pride and Prejudice
They talk about Mr. Darcy and Elizabeth Bennet, and critics have noted the parallels in the Fox-Kelly sparring.
Q 20Which actress turned down the role of Kathleen Kelly?
Julia Roberts
She lacked confidence in the quality of romantic-comedy scripts at the time.
The neighborhood's cafés, parks and brownstones are practically a supporting character.
Q 24What was the film's production budget?
$65 million
It grossed $250.8 million worldwide, making it the director's highest-grossing film despite mixed reviews.
Q 25Which film did You've Got Mail beat to open at number one in North America?
The Prince of Egypt
It earned $18.4 million on its opening weekend after a December 18, 1998 release.
Q 26Which studio released the film in December 1998?
Warner Bros.
It came out on December 18, in time for the holiday season the film so lovingly photographs.
Q 27The soundtrack leans heavily on the work of which singer-songwriter?
Harry Nilsson
It mixes 1950s and 1970s classics with new recordings, plus an orchestral score by an English composer.
Q 28Who composed the film's score?
George Fenton
The English composer's music sits alongside the soundtrack's pop classics.
Q 29What approval rating did You've Got Mail hold on Rotten Tomatoes as of 2025?
70%
The consensus praised the chemistry between the leads; Metacritic's score was a middling 58.
Q 30The film's original promotional website stayed online until at least which year?
2018
It became a favorite example for people mocking 1990s web design.