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The following FAQ entries may contain spoilers. Only the biggest ones (if any) will be covered with spoiler tags. Spoiler tags are used sparingly in order to make the page more readable.
For detailed information about the amounts and types of (a) sex and nudity, (b) violence and gore, (c) profanity, (d) alcohol, drugs, and smoking, and (e) frightening and intense scenes in this movie, consult the IMDb Parents Guide for this movie. The Parents Guide for Sleepless in Seattle can be found here.
When Sam Baldwin (Tom Hanks) loses his wife Maggie to cancer, his 8-year-old son Jonah (Ross Malinger), concerned that Sam is still grieving after 18 months and a move from Chicago to Seattle, contacts a national radio talk show and asks the host to help him find a new mother. The response is so great that Sam's mailbox is filled with hundreds of women wanting to meet him, but the only one who passes Jonah's inspection is a letter from Annie Reed (Meg Ryan), a newspaper writer in Baltimore, Maryland, who offers to meet them on top the Empire State Building on Valentine's Day, just like in the movie An Affair to Remember (1957). Unfortunately, Sam prefers to meet women the old-fashioned, "magical" way that worked for him and Maggie and has no interest in meeting this Annie Reed.
The screenplay for Sleepless in Seattle was written by American screenwriters David S. Ward and Jeff Arch along with the movie's director Nora Ephron. However, the film was inspired by the 1957 film An Affair to Remember, in which a man and woman fall in love and plan to meet in six months on the Empire State Building in New York City. Clips from An Affair to Remember are shown in the movie, and the characters frequently discuss the film.
When Jonah and Sam speak with the talk show hostess, Dr Marcia Fieldstone (Caroline Aaron, it comes out that Sam is still having trouble sleeping at night, so Fieldstone refers to him as 'Sleepless in Seattle' rather than calling him by name.
After breaking up with Walter (Bill Pullman), Annie notices a lighted heart on the face of the Empire State building. Considering it a sign, she rushes over, hoping that Sam might still be there. Unfortunately, she arrives at the building after the last elevator run to the deck but convinces the doorman to let her go up. Meanwhile, Sam is reunited with Jonah on the observation deck, and they are on their way down, but Jonah realizes that he left his backpack on the deck. They return to fetch it and find Annie holding it. Sam and Annie recognize each other immediately, having seen each other before in the airport and on the street, and the "magic" happens. In the final scene, Sam offers his hand to Annie, and the three of them leave the observation deck together.
It's interesting to note that, outside of the romantic comedy genre and without an adorable and unthreatening actress like Meg Ryan in the lead role, Sleepless in Seattle appears to be a movie about a woman stalking a man she's never met. As ScreenPrism notes, many of Annie's actions (hiring a private investigator, flying across the country, getting jealous of people in a stranger's life) would be considered majorly creepy by most people in real life.
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