How Well Do You Know "Sleepless in Seattle," "When Harry Met Sally..." and "You've Got Mail"?



By: Jane Andrews

6 Min Quiz

Image: TriStar Pictures

About This Quiz

You can't be a fan of romantic comedies and not love Nora Ephron. The screenwriter and director was a master of the feel-good movie genre, as well as a pioneering female force in a field that had previously been dominated by men. Before Ephron made a major impression on Hollywood, she was an accomplished reporter and essayist. In 1983, she wrote the autobiographical novel "Heartburn," and earned her first screenwriting credit for the film "Silkwood" starring Meryl Streep. She also wrote the screenplay for the 1986 movie version of her book, which earned her an Academy Award nomination for Best Original Screenplay.

But it wasn't until Ephron wrote a little film called "When Harry Met Sally," released in 1989, that her supreme talent for creating witty, happily-ever-after flicks became clear. The script won her another Academy Award nomination, as did her screenplay for the swoon-worthy 1993 film "Sleepless in Seattle," which she also directed. Five years later, Ephron sealed her legacy as the queen of the rom-com when she wrote and directed "You've Got Mail." Audiences have been enjoying these movies ever since.

How well do you remember these three heart-melting and hilarious movies? Get ready to experience all the warm-feels and find out by taking this quiz!

Where does Annie ask Sam to meet her in "Sleepless in Seattle"?

In the movie's famous final scene, Meg Ryan and Tom Hanks are not really on the roof of the Empire State Building. They're actually filming in an airline hangar in Seattle that was built to look like the New York City landmark.


Who played Harry in "When Harry Met Sally"?

Crystal began his acting career on TV, where he starred on the hit sitcom "Soap" from 1977 to 1981. He was also a "Saturday Day Night Live" cast member during the 1984 to 1985 season.


What's the name of Tom Hanks's character in "Sleepless in Seattle"?

During the making of "Sleepless in Seattle," Hanks reportedly used his days off to do voice work for the character of Woody in the first "Toy Story" film. "Toy Story" was released in 1995, two years after "Sleepless in Seattle."


Where does "You've Got Mail" take place?

The majority of "You've Got Mail" was filmed on location on Manhattan's Upper West Side. Reportedly, Ephron chose the neighborhood to serve as the movie's setting because she said it felt like a small village.


Which of the following actresses starred in "When Harry Met Sally," Sleepless in Seattle" and "You've Got Mail"?

In a 2015 Vanity Fair article, Ryan said of Ephron, "She had such a sweetness. There was all that laceyness about her, and unbelievable sweetness, and then she was such a powerhouse. Such a powerful thinker and such a strong person."


Which actress plays Suzy, Sam's sister, in "Sleepless in Seattle"?

Despite playing his sibling in this film, actress and singer Rita Wilson has been married to Tom Hanks since 1988. The pair first met on the set of the sitcom "Bosom Buddies" in the early '80s, and fell in love when they starred together in the 1985 comedy "Volunteers."


Who says the following line from "You've Got Mail"? "It's a lovely store, and in a week it will be something really depressing, like a Baby Gap."

Kathleen writes this in one of her emails to Joe, lamenting over the fact that she has to close her book shop. "Soon we'll just be a memory," she adds "In fact, someone, some foolish person, will probably think it's a tribute to this city, the way it keeps changing on you, the way you can never count on it, or something."


During the car trip to New York in "When Harry Met Sally," what does Harry say he believes men and women can never do?

Harry tells an incredulous Sally, "What I'm saying is — and this is not a come-on in any way, shape or form — is that men and women can't be friends because the sex part always gets in the way."


Can you tell us what Kathleen's screen name was in "You've Got Mail"?

Fun fact: All of the emails written between Kathleen and Joe were featured on the movie's official website, which has been archived and can still be accessed today (just go to


Which "When Harry Met Sally" character said, "When I buy a new book, I read the last page first. That way, in case I die before I finish, I know how it ends."

During their car ride from the University of Chicago to New York City, Harry says this to Sally in an attempt to prove just how dark he believes his dark side to be. "That doesn't mean you're deep or anything," she retorts.


Which actress played Sally's best friend Marie in "When Harry Met Sally"?

While Fisher has become a pop culture icon for her role as Princess Leia in the "Star Wars" films, she appeared in several notable comedies, including "The 'Burbs" and "Soap Dish." She was also an accomplished author and screenwriter.


"When Harry Met Sally" was written by Nora Ephron. Who directed the film?

Reiner first worked with Billy Crystal back in 1975 when the actor turned director starred as Mike Stivic on the sitcom "All in the Family." Crystal was cast as Mike's best friend, and the two hit it off instantly.


Do you remember the name of the bookstore chain Joe runs in "You've Got Mail"?

Reportedly, "You've Got Mail" producers asked Barnes & Noble if they could use one of their New York City locations to serve as the fictional Fox Books store, but the chain declined.


Can you finish this quote from "Sleepless in Seattle? "Destiny is something that we've invented because we can't stand that fact that everything that happens is __________."

"Sleepless in Seattle" was a huge hit when it was released in1993. It hit number two at the box office the weekend it opened, behind the blockbuster "Jurassic Park." In total, the film grossed more than $227.8 million worldwide.


In "When Harry Met Sally," which of the following lines is said by a fellow diner after Sally fakes an orgasm in a restaurant?

The older woman who delivers this famous quote is Estelle Reiner, director Rob Reiner's mother. To show Meg Ryan how he wanted her to play the scene, Reiner performed his own version of orgasm-faking, which he had to do in front of his mother.


Different versions of which of the following songs are featured in both "Sleepless in Seattle" and "You've Got Mail"?

In "Sleepless in Seattle," a jazz version of "Somewhere Over the Rainbow" plays after Tom Hanks calls into the radio station for the first time. A version of the song by George Fenton plays in the final scene of "You've Got Mail" when Kathleen and Joe meet in the garden.


When Harry and Sally bump into each other on a plane flight in an early "When Harry Met Sally" scene, how many years has it been since their car ride to New York?

Harry and Sally do not become friends until five years after this plane flight when they run into each other in a New York City book store. The rest of the events in the film unfold over the following two years.


In "You've Got Mail," what's Kathleen's favorite book?

In one of her emails to NY152, Kathleen writes, "Confession: I have read 'Pride and Prejudice' two hundred times. I get lost in the language, words like: Thither. Mischance. Felicity. I am always in agony over whether Elizabeth and Mr. Darcy are really going to get together."


What's the name of the friend in "Sleepless in Seattle" who mails Annie's letter to Sam?

Played by the hilarious Rosie O'Donnell, Becky is Annie's editor and best friend. "Sleepless in Seattle" also features an appearance by Rob Reiner, who directed "When Harry Met Sally."


Do you remember the name of Harry's best friend in "When Harry Met Sally"?

Jess was played by Bruno Kirby, who also starred alongside Billy Crystal in the 1991 hit comedy "City Slickers." Sadly, the actor died in 2006 due to complications related to leukemia. He was 57 years old.


What's the name of Kathleen's bookstore in "You've Got Mail"?

The name for the bookstore was inspired by a 1940 romantic comedy starring Margaret Sullavan and James Stewart called "The Shop Around the Corner." That movie takes place in a leather goods shop.


After Annie announces her engagement to Walter in "Sleepless in Seattle," what happens to him?

Walter is played by actor Bill Pullman, who starred alongside Sandra Bullock in another popular rom-com from the 1990s, "While You Were Sleeping." In that movie, he played the romantic lead and got the girl.


In "You've Got Mail," Joe tells Kathleen he believes this film has the answers to all of life's questions. Which is it?

Released in 1972, "The Godfather" was directed by Francis Ford Coppola and featured legendary performances from actors like Marlon Brando, Al Pacino, James Caan and Robert Duvall. It was followed by "The Godfather Part II" in 1974 and "The Godfather Part III" in 1990.


In "Sleepless in Seattle," which movie prompts Annie to write her letter to Sam?

Released in 1957, "An Affair to Remember" stars Cary Grant and Deborah Kerr as star-crossed-lovers Nickie Ferrante and Terry McKay. It's a remake of a 1939 film called "Love Affair." Leo McCarey directed both films.


Can you recall the song Harry and Sally sing on the karaoke machine in The Sharper Image store in "When Harry Met Sally"?

"The Surrey with the Fringe on Top" is a well-known show tune from the 1943 Rodgers and Hammerstein stage musical "Oklahoma!" The song also appears in the film version, which was released in 1955.


When Joe visits Kathleen's store for the first time in "You've Got Mail," what gets stuck in the door?

According to DVD commentary from the film, the balloons getting stuck in the door was an accident. But because Tom Hanks then ad-libbed the funny line, "Good thing it wasn't the fish," Ephron decided to keep the scene in the movie.


In "When Harry Met Sally," Harry claims there are two types of women — high maintenance and low maintenance. Which does he believe Sally to be?

"You're the worst kind," Harry tells Sally. "You're high maintenance, but you think you're low maintenance." When Sally says she doesn't think this is true, he begins to recite the nit-picky way in which she orders food in restaurants.


Do you remember the name of Joe's date in "Sleepless in Seattle"?

While Nora Ephron directed a move called "This Is My Life" in 1992, "Sleepless in Seattle" was her first big hit as a director. She wrote "When Harry Met Sally," but did not direct the film.


Do you remember the name of Sam's late wife in "Sleepless in Seattle"?

After Maggie tragically passes away due to cancer, Sam and his son, Jonah, move from Chicago to Seattle to start anew. The events of the film take place a year and a half after Maggie's death.


What does Annie do for a living in "Sleepless in Seattle"?

Meg Ryan must enjoy playing writers — Annie is a reporter for the Baltimore Sun in "Sleepless in Seattle," and Sally is a journalist for the fictional publication The News in "When Harry Met Sally."


In "When Harry Met Sally," Marie forces Jess to throw out an ugly piece of furniture. What is it?

Upset after running into his ex-wife, Harry warns Jess and Marie to keep track of their stuff before getting married. "Because someday, believe it or not, you'll go 15 rounds over who's gonna get this coffee table," he says. "This stupid, wagon wheel, Roy Rogers, garage sale coffee table!"


What was the name of Harry's ex-wife in "When Harry Met Sally"?

Helen was played by actress Harley Jane Kozak, who also appeared in the popular films "Parenthood" and "Arachnophobia." She's also an accomplished writer and has published five mystery novels.


Do remember the name of Joe's dog in "You've Got Mail"?

If you look carefully, you'll see that Brinkley is the subject line Joe uses in his first email to Kathleen. And in the film's final scene, Kathleen sees the golden retriever before Joe is revealed to be her online suitor.


What does Kathleen say to Joe at the end of "You've Got Mail?

Kathleen says this to Joe when they meet in the garden, and she realizes he's the man she's been corresponding with online. They are the last words of the movie and are often quoted as a favorite rom-com line.


Where does Harry finally declare his love to Sally in "When Harry Met Sally"?

In what may be one of the sweetest lines of the movie, Harry tells Sally, "I came here tonight because when you realize you want to spend the rest of your life with somebody, you want the rest of your life to start as soon as possible."


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