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60 free Sleepless in Seattle trivia questions with answers — entertainment quiz, new questions added Aug 2026.
54 free Sleepless in Seattle trivia questions with answers. This Sleepless in Seattle trivia quiz digs into every corner of Nora Ephron's 1993 romantic comedy. It starts with the story you remember - Sam and Jonah on the Lake Union houseboat, Annie at the Baltimore Sun, the Christmas Eve radio call, the letter Becky mails behind Annie's back and the Valentine's Day meeting on the Empire State Building - then moves behind the camera to the years of rejected drafts, the casting near-misses, the six hours Leona Helmsley granted at the real skyscraper and the replica observation deck built in a Seattle naval hangar. There are questions on the soundtrack that hit number one, the two Oscar nominations, the opening weekend behind Jurassic Park, the film's debt to An Affair to Remember, the tiramisu craze it started and the stage musical it eventually became. Roughly a third of the questions are warm-ups any fan will get; the rest climb toward details only someone who has read every Ephron interview would know. Every answer has been checked against Wikipedia and the sources it cites, and each explanation adds one more thing worth knowing about the movie.
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Q 01What does Sam Baldwin do for a living?
Architect
Sam has moved to a new city to start over after his wife's death, and his profession gives him a plausible reason to design his own new life from scratch.
Q 02Annie Reed is a reporter for which newspaper?
The Baltimore Sun
Her job gives her the pretext for a work trip west once she becomes curious about the widower she heard on the radio.
Q 03On which night does Jonah first call the radio talk show about his father?
Christmas Eve
Although the film is now a Valentine's Day staple, it also passes through Christmas and New Year's Eve along the way.
Q 04What is the name of the radio host who takes Jonah's call?
Dr. Marcia Fieldstone
The host is voiced by Caroline Aaron; the film's writer-director gave herself a cameo as another late-night caller.
Q 05What was the name of Sam's late wife?
Maggie
She is played in flashback by Carey Lowell, and Sam tells the radio audience he knew she was the one the first time he took her hand.
Q 06From which city do Sam and Jonah move to Seattle?
Chicago
Ephron said she chose Seattle because it struck her as a city where people had chosen lifestyle over work, the opposite of the work-focused town Sam leaves behind.
Q 07Which actress plays Sam's sister Suzy, a part she landed after auditioning for a different role?
Rita Wilson
She originally read for Annie's best friend, but the director preferred her as the sister and found it convenient that she was already in Seattle with her husband, Tom Hanks.
Q 08Which child actress plays Jonah's friend Jessica, who books his flight to New York on her mother's computer?
Gaby Hoffmann
She had made her film debut a few years earlier as the farmer's daughter in Field of Dreams and had also appeared in Ephron's directorial debut.
Q 09Rob Reiner's character Jay mentions which dessert to Sam, who mistakes it for a euphemism?
Tiramisu
The scene is credited with introducing much of America to the dessert; the studio reported 20 to 30 phone calls a day from viewers asking what it was.
Q 10An Affair to Remember, the 1957 weepie the film's women keep watching, paired Cary Grant with which actress?
Deborah Kerr
Her singing voice in the film was dubbed by Marni Nixon, the same vocalist who later dubbed her in The King and I and Natalie Wood in West Side Story.
Q 11An Affair to Remember remade a 1939 Leo McCarey film pairing Charles Boyer with which actress?
Irene Dunne
That earlier film, Love Affair, used the very same screenplay almost scene for scene, and Warren Beatty and Annette Bening remade it yet again in 1994.
Q 12Which struggling writer conceived the story in 1989 and shares screenplay credit on the film?
Jeff Arch
It was his first script ever optioned, and it began life as a play about two people falling in love over the telephone without meeting.
Q 13Which co-writer, hired to rewrite the script, had earlier won an Oscar for writing The Sting?
David S. Ward
Q 21Rosie O'Donnell modelled her performance as Becky on which entertainer's walk and talk?
Bette Midler
She wanted to play the funny, caustic best friend with a heart of gold, and her big speech was the longest of her career to that point.
Q 22Nora Ephron voices which late-night caller to the radio show?
Disappointed in Denver
Producer Gary Foster also sneaks in as an extra in the restaurant on Sam and Victoria's first date, where Hanks accused him of being too loud.
Q 23Which actress, cut from Sleepless in Seattle, got an apologetic letter from Ephron and a bigger part in You've Got Mail?
Parker Posey
His biggest structural change was having the son, not the father, call the radio station, arguing no self-respecting man would phone in his grief voluntarily.
Q 14Which director, reassigned after being removed from Hook, quit over Ephron's less sentimental rewrite?
Nick Castle
By coincidence, his own film Dennis the Menace opened on the very same day as Sleepless in Seattle in June 1993.
Q 15Sleepless in Seattle was Nora Ephron's second film as director. What was her first?
This Is My Life
That 1992 comedy-drama lost money, which is why Ephron was hunting for quick script-doctoring work when this project came along.
Q 16Hanks and Ryan had already played a couple in which earlier film?
Joe Versus the Volcano
In that 1990 oddity Ryan played three different roles; the pair would reunite for a third time in You've Got Mail.
Q 17Meg Ryan initially expected to star opposite which actor, her husband at the time?
Dennis Quaid
Ephron felt he was not funny enough for Sam, and the studio agreed the part suited Hanks better.
Q 18The original screenwriter wrote Annie for Meg Ryan, but which actor had he pictured as Sam?
Kevin Costner
Once Ephron signed on, a queue of stars including Julia Roberts, Michelle Pfeiffer and Madonna chased the Annie role, but Ephron never wavered from Ryan.
Q 19Which child actor was originally cast as Jonah before being replaced by Ross Malinger?
Nathan Watt
Hanks found the first choice disruptive on set after a few days; Jason Schwartzman was among the others who had auditioned.
Q 20Rosie O'Donnell had made her film debut the previous year alongside Hanks in which movie?
A League of Their Own
She credits Ephron's son Jacob Bernstein, a fan of her friend Madonna, with helping her land the part of Becky.
In You've Got Mail she plays Patricia, the high-strung girlfriend of Hanks's bookstore magnate.
Q 24In Sleepless in Seattle, Hanks and Victor Garber fake-weep over which war film, mocking tears for An Affair to Remember?
The Dirty Dozen
Ephron generally wanted lines delivered as written, but she credited Hanks with helping rewrite Sam into a grumpier, funnier character.
Q 25Sam's houseboat sits on which Seattle body of water?
Lake Union
Floating homes line both its east and west shores; the film's writer got the idea after seeing a similar Seattle home on a home-renovation TV show.
Q 26The writer got the idea of putting Sam in a houseboat from a Seattle episode of which TV series?
This Old House
Host Bob Vila had toured a similar floating home on the show; the writer's other inspirations included a Tony Robbins seminar and a French film.
Q 27Where was the Empire State Building observation deck for the climactic meeting actually built?
A hangar at a Seattle naval base
Seattle had no proper sound stages, so the crew took over Sand Point Naval Base as it was closing; the real building was digitally lit for the exterior.
Q 28Which imprisoned building owner granted just six hours to shoot at the Empire State Building?
Leona Helmsley
Ephron knew the owner's publicist, who raised it during a jail visit; the six hours covered the helicopter shot, the lobby scene and Jonah's search of the deck.
Q 29Which former Navy Secretary senator did Ephron call to secure the naval base for filming?
John Warner
The federal bureaucracy had ignored the production until she went straight to the top; the base was about to shut down.
Q 30Which legendary Swedish cinematographer, a longtime Ingmar Bergman collaborator, shot the film?
Sven Nykvist
Ephron had been told to hire the world's best; she said he could light a scene in as little as six minutes.