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Sleepless in Seattle
Architect Sam Baldwin moves from Chicago to Seattle with his eight-year-old son, Jonah, to start a new life following the death of his beloved wife, Maggie. Over a year later, on Christmas Eve, Jonah calls a nationally syndicated radio talk show seeking advice on how to help his father find happiness again. He persuades a reluctant Sam to go on the air and talk about how much he misses Maggie. Sam describes her as his soulmate, explaining that he knew she was the one when he first took her hand and believes he could never find true love twice. Touched by his story, thousands of women across the country write to him.
One listener is Annie Reed, a Baltimore Sun reporter. She is engaged to the sensible and supportive Walter, but feels something is missing from their relationship. Her friend and editor, Becky, suggests Annie longs for the kind of destined romance found "in a movie", although Annie dismisses the idea of magical love or fate. Inspired by the romance film An Affair to Remember, Annie writes Sam a letter proposing they meet atop the Empire State Building in New York City on Valentine's Day. She decides against sending it, but Becky secretly mails it.
Encouraged by the response to his radio appearance and by his friends, Sam begins dating a co-worker, Victoria, whom Jonah vehemently dislikes. When Jonah reads Annie's letter, he instinctively believes she could be the one for his father, but Sam dismisses the idea because of the distance between Seattle and Baltimore. Jonah's friend Jessica urges him to reply on Sam's behalf, agreeing to the meeting. After Jonah calls the radio show again and reveals that Sam is dating, Annie travels to Seattle on a work assignment arranged by Becky as a pretext to learn more about him.
While dropping Victoria off at the airport, Sam notices Annie leaving her flight and is immediately captivated by her, unaware of who she is. Later, Annie secretly watches Sam and Jonah playing together on the beach. The following day, she visits Sam's houseboat but mistakes his sister, Suzy, for Victoria. A passing vehicle nearly strikes Annie and sounds its horn, alerting Sam to her presence. They briefly stare at one another before Annie, embarrassed, leaves.
Back in Baltimore, Annie reads Jonah's immature reply and concludes she has made a mistake pursuing Sam. She decides to commit to Walter and travel to New York to meet him on Valentine's Day. Meanwhile, Jessica uses her travel agent mother's computer to book Jonah a flight to New York to find Annie. When Sam learns where Jonah has gone, he flies after him, and they reunite on the Empire State Building's observation deck.
During dinner with Walter, Annie confesses her doubts about their relationship, everything that has happened since hearing Sam's radio broadcast, and they amicably end their engagement. Seeing the Empire State Building illuminated in the shape of a heart, Annie takes it as a sign. She rushes there, arriving on the observation deck moments after Sam and Jonah have left in the elevator.
When Sam and Jonah return to retrieve Jonah's misplaced backpack, Sam and Annie recognize each other. After introducing themselves, Annie takes Sam's hand, and the three leave together.