In spite of the observation deck being deserted, Annie convinces the elevator operator to let her take a quick look around. Annie convinces the guard to let her go to the observation deck after mentioning An Affair to Remember (which the guard replies is his wife's favorite movie) and arrives just moments after the doors to the down elevator close with Sam and Jonah inside. She rushes to the Empire State Building but is told that the observation deck is closed. Meanwhile, Annie has seen the skyscraper from the Rainbow Room where she is dining with Walter and confesses her doubts to him. Sam, distraught, follows Jonah and finds him on the observation deck. Jonah goes to the observation deck and asks every unattached woman if she is Annie. With Jessica's help, Jonah flies to New York without Sam's permission and goes to the Empire State Building searching for Annie. She decides she is being foolish and goes to New York to meet Walter for Valentine's Day. He recognizes her from the airport and says 'Hello', but Annie can only respond with another 'Hello' before fleeing. Annie watches Sam and Jonah playing on the beach together but mistakes Sam's sister Suzy ( Rita Wilson) for his girlfriend. While dropping Victoria off at the airport for a flight, Sam sees Annie exiting from her plane and is taken by her, although he has no idea who she is. On the advice of his friend Jessica ( Gaby hoffmann), Jonah replies to Annie, agreeing to the New York meeting. Jonah, a baseball fan, reads Annie's letter and likes that it mentions the Baltimore Orioles, but he fails to convince his father to go to New York to meet Annie.

Sam begins dating a co-worker, Victoria ( Barbara Garrick), whom Jonah dislikes. She does not intend to mail it, but her friend and editor Becky ( Rosie O'Donnell) does it for her and agrees to send Annie to Seattle to 'look into doing a story on those radio shows'. After watching the film An Affair to Remember, Annie impulsively writes a letter suggesting that Sam meet her on top of the Empire State Building on Valentine's Day. She is engaged to Walter ( Bill Pullman) but feels there is something missing from their relationship. One of the listeners is Annie Reed ( Meg Ryan), a Baltimore Sun reporter. Hundreds of women from around the country hear the program and touched by the story, write to Sam.

Jonah persuades Sam to go on the air to talk about how much he misses Maggie. He and his young son Jonah ( Ross Malinger) start anew in Seattle, Washington, USA, but Sam continues to grieve.Ī year and a half later, on Christmas Eve 1992, Jonah-who wants his father to find a new wife-calls in to a radio talk show. Sam Baldwin ( Tom Hanks), a Chicago architect, loses his wife Maggie ( Carey Lowell) to cancer.

Sleepless in