Sleepless in Seattle (1993)
After his wife Maggie passes away, Sam Baldwin and his 8-year-old son Jonah relocate from Chicago to Seattle to escape the grief associated with Maggie's death. Eighteen months later Sam is still grieving and can't sleep. Although Jonah misses his mother, he wants his father to get a new wife despite Sam having not even contemplated dating again. On Christmas Eve, Sam (on Jonah's initiative) ends up pouring his heart out on a national radio talk show about his magical and perfect marriage to Maggie, and how much he still misses her. Among the many women who hear Sam's story and fall in love with him solely because of it is Annie Reed, a Baltimore-based newspaper writer. Annie's infatuation with Sam's story and by association Sam himself is despite being already engaged. But Annie's relationship with her straight-laced fiancé Walter is unlike her dream love life in the movie An Affair to Remember (1957). She even writes to Sam proposing they meet atop the Empire State Building on Valentine's Day. Back in Seattle, Sam has received hundreds of letters from women wanting to meet him. Jonah is excited by one letter in particular from Baltimore and will do whatever he needs to to get his father and Annie together. However, old fashioned Sam wants his future love life to be based on meeting a woman the traditional way and he, in turn, becomes infatuated with an unknown woman he spots a few times in Seattle. Will magic happen twice in Sam's life, and if so will it be with this unknown woman or Annie?
Sam is a recent widower who is seeking someone new. Sam's son Jonah, is also looking for a new mother, so when Jonah puts his father on national radio, hundreds of women write to him. One of the women is Annie. She's engaged to Walter, but he's a bit strange. Annie goes to great lengths to meet Sam.
After his wife died, Sam Baldwin did not think about other women. His 8-year old son Jonah thinks that his father needs a woman in order to get his life back in order and calls in on a nation-wide radio-show. The voice and story of Sam is heard by hundreds of women, including Annie Reed, who is about to marry her fiancé Walter soon. She can't find a rest until she really knows for sure that Sam Baldwin is not the one person for her. Thus, Annie travels to Seattle, where Sam and Jonah live, and there decides that Sam is not the one. The letter she never sent was posted by a friend of Annie, and therefore Jonah, who feels that she's the one for his dad, already booked a flight to New York in order to meet her on the roof of the Empire State building, just like in "An Affair to Remember". Of course, his father follows him instantly...
When Sam Baldwin's wife dies, he decides to move to Seattle with his son, Jonah. When Jonah sees how sad his father is, he calls a radio psychiatrist, who dubs him Sleepless in Seattle cause Jonah says he can't sleep. He starts to talk about his wife and women over the country hear his tale and one woman Annie who lives in Baltimore can't help but fascinated by his tale. Annie despite being engaged can't stop thinking of Sam and soon tries to find all she can about she even goes to Seattle to see him. And once she gets off the plane, Sam who was in the airport to see someone off, sees her and can't keep his eyes off her and tries to follow her but couldn't catch her. Jonah who has been going through the mail that his father has gotten ever since he was on the radio, sees the letter Annie wrote on a whim but didn't send it but her friend did. He tells his father this could be it. But Sam doesn't think he could have a relationship with someone who lives so far away.
A recently widowed man's son calls a radio talk-show in an attempt to find his father a partner.
- Sam Baldwin, a Chicago architect, has lost his wife (Carey Lowell) to cancer. He counsels his 8 year old son, Jonah (Ross Malinger), that it's hard to understand why she had to die, warning his son that if a person starts asking that question, they just go crazy.
Sam decides he and Jonah should move to Seattle, Washington to make a fresh start. Sixteen months later Sam is still disconsolate and Jonah is worried. So, on Christmas Eve, Jonah calls Dr. Marcia Fieldstone, a clinical psychologist who hosts a national radio talk show, and he requests a new wife for his father. Dr. Fieldstone persuades Jonah to put Sam on the phone. Sam is upset, but he talks to Dr. Fieldstone about how he's been taking it a day at a time and that he's not sure he could ever love another woman. He admits that it would be best if Jonah had a mother figure. When Dr. Fieldstone learns that Sam has trouble sleeping, she decides to refer to him as Sleepless in Seattle.
Thousands of women around the country, touched by the sad story of Sleepless in Seattle, send him letters (Jonah secretly provides Dr. Fieldstone with the address). Annie Reed, a journalist from Baltimore, Maryland, engaged to a nice but allergy-prone man named Walter (Bill Pullman), also hears the show with Dr. Fieldstone. Annie has been having doubts about her future with Walter and she begins to wonder about a possible connection between her and Sam. She actually drafts a letter to Sam, but decides not to send it. Her friend and co-worker, Becky (Rosie O'Donnell) secretly sends it to Sam.
Jonah, who has been working his way through the flood of mail, finds Annie's missive and thinks the fact that shes a fan of Brooks Robinson of the Baltimore Orioles is a "sign." The movie includes a number of such signs or omens. Jonah tries to convince his father to go to New York City to meet Annie at the top of the Empire State Building on Valentine's Day (as her letter suggested), but Sam says no, it's too far away.
Sam has resisted dating anyone, but after he comes home from work one afternoon to find Jonah sitting very close and listening to records with a precocious young girl named Jessica (Gaby Hoffmann), he feels an urgent need to try and find a mother-type for Jonah. Sam thinks it's probably best to associate with women he already knows, so he calls an acquaintance from work, Victoria (Barbara Garrick), and arranges a date.
Jonah immediately dislikes Victoria her, because he didn't select her (he wants Sam to meet Annie) and she has a cackling, hyena-like laugh. On the advice of Jessica, Jonah mails a letter to Annie, pretending to be Sam and agreeing to meet her at the top of the Empire State Building on Valentine's Day. Annie decides to do a news story on Sleepless in Seattle, and she tells Walter that she needs to travel to Chicago to do an interview for the story. She then flies out to Seattle.
Coincidentally, Sam and Jonah are at the airport in Seattle, dropping Victoria off for a flight, and Annie arrives at the same gate. Sam sees her and is immediately attracted, however she quickly disappears into the crowd.
Annie rents a car and drives to Sam's house. Sam and Jonah have returned from the airport and are just taking a small boat out for a ride. Annie is able to follow them in her car, as they stay close to land. She watches Sam and Jonah playing on the beach together, but she doesn't try to approach them. She talks to Becky about it that night and decides that the next day, she will go up and talk to Sam. The next day, she gets out of her car and starts across the street, but stops short when she sees Sam and Jonah hugging Sam's sister, who came to visit. A truck driver blasts his horn at Annie, as she's standing in traffic. Sam looks up, sees her, and approaches her. They exchange hellos. Rather than wait for traffic to clear and go on across the street, Annie decides she is being silly about the whole thing, that Sam obviously has a girlfriend, and she goes back to New York and Walter.
Jessica decides that Jonah should go to New York by himself to meet Annie, since Sam won't go. She then calls and makes the flight reservation. Jonah manages to get to New York and takes a taxi to the Empire State Building, telling the driver that he's going to meet his new mother. Once Sam finds out from Jessica where Jonah went, he rushes off in pursuit. He doesn't catch up to Jonah until he gets to the observation deck of the Empire State Building, where Jonah has been patiently waiting for Annie to appear.
Meanwhile, Annie is at dinner with Walter at a high rise across the way. She's explaining the entire Sleepless in Seattle story to Walter. Walter doesn't want to be someone that Annie settles for in life, so he agrees to take back the ring he had given her. Annie then hurries on over to the Empire State Building just in case Sam's letter was legitimate.
Jonah and Sam get on the down elevator just as Annie is exiting the elevator she's on. They miss each other. However, Annie discovers Jonah's backpack with Howard, his teddy bear, inside. As she's pondering that, Jonah and Sam come back out to the observation deck to retrieve the backpack, and they see and meet Annie for the first time.
Sam notices the guard getting antsy, as the observation floor is officially closed, and says "we'd better go", then holds out his hand to Annie and adds, shall we?
Jimmy Durante is singing Make Someone Happy as the camera pans around the outside of the Empire State Building, with the windows lit up like red hearts on each side, then the scene draws way back into space so that we see an outline of the entire U.S. with fireworks shooting high above as the movie ends.