Sam, in Seattle, grieves for his lost wife. Annie, in Baltimore, is engaged to the perfect man. For her the passion is missing in their relationship. One fateful Christmas Eve, she is listening to the car radio as Sam tells the story of his love for his wife and a wish to meet someone like her.
Annie is touched by his story. She wants to meet him and write his story for her newspaper. When Sam receives her letter, he ignores it as he has the hundreds of other letters women have written. Sam's son reads them and decides he wants Annie to be his step-mother.
Plotting with his best friend, Sam's son, Jonah, manages to board a plane for New York City. He has written to Annie and told her Sam will meet her at the top of the Empire State Building on Valentine's Day. This is the story of that meeting.