In spite of the observation deck being deserted, Annie discovers a backpack that Jonah left behind.

She rushes to the Empire State Building just moments after the doors to the down elevator close with Sam and Jonah inside. Meanwhile, Annie sees the skyscraper from the Rainbow Room where she is dining with Walter and confesses her doubts to him, amicably ending their engagement. Distraught, Sam follows Jonah and finds him on the observation deck. With Jessica's help, Jonah flies to New York without his father'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 only responds with another 'Hello' before fleeing. Annie later secretly watches Sam and Jonah playing on the beach together but mistakes Sam's sister for his girlfriend. While dropping Victoria off at the airport for a flight, Sam sees Annie exiting from her plane and is mesmerized by her, although he has no idea who she is. On the advice of his playmate Jessica, 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, whom Jonah dislikes. She does not intend to mail it, but her friend and editor Becky does it for her and agrees to send Annie to Seattle. 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. One of the listeners is Annie Reed, a Baltimore Sun reporter who is engaged to amiable Walter but feels there is something missing from their cordial relationship. Hundreds of women from around the country who hear the program and are touched by the story write to Sam.

Jonah persuades a reluctant Sam to go on the air to talk about how much he misses Maggie. A 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. He and his eight-year-old son Jonah start a new life in Seattle, Washington, but Sam continues to grieve. Chicago architect Sam Baldwin loses his wife Maggie to cancer.

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