After Chicago architect Sam Baldwin loses his wife Maggie to cancer, he and his eight-year-old son Jonah start a new life in Seattle, but they continue to grieve. A year and a half later on Christmas Eve, Jonah calls in to a radio talk show. Jonah persuades a reluctant Sam to go on the air to talk about how much he misses Maggie. Hundreds of women from around the country who hear the program and are touched by the story write to Sam. One of the listeners is Annie Reed, a Baltimore Sun reporter who is engaged to Walter but feels there is something missing from their relationship. After watching the film An Affair to Remember, Annie writes a letter suggesting that Sam meet her on top of the Empire State Building on Valentine's Day. She decides not to mail it, but her friend and editor Becky does it for her and later agrees to send Annie to Seattle to find her a new partner.