Sam Baldwin, a Chicago architect, has lost his wife (Carey Lowell) to cancer. He counsels his 8 year old son, Jonah (Ross Malinger), that its 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 hes been taking it a day at a time and that hes 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 ODonnell) 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, its 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 whom he already knows, so he calls an acquaintance from work, Victoria (Barbara Garrick), and arranges a date.Jonah immediately dislikes Victoria her, because he didnt 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 Sams house. Sam and Jonah had 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 doesnt 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 Sams sister, who came to visit. A truck driver blasts his horn at Annie, as shes 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 wont 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 doesnt 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. Shes explaining the entire Sleepless in Seattle story to Walter. Walther doesnt 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 Sams letter was legitimate.Jonah and Sam get on the down elevator just as Annie is exiting the elevator shes on. They miss each other. However, Annie discovers Jonah's backpack with Howard, his teddy bear, inside. As shes pondering about 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 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.
Output: Question: What is Annie doing with Walter?, Answer: Dinner