When Sam Baldwin's wife dies, he decides to move to Seattle with his son, Jonah. When Jonah sees how sad his father is, he calls a radio psychiatrist, who dubs him Sleepless in Seattle cause Jonah says he can't sleep. He starts to talk about his wife and women over the country hear his tale and one woman Annie who lives in Baltimore can't help but fascinated by his tale. Annie despite being engaged can't stop thinking of Sam and soon tries to find all she can about she even goes to Seattle to see him. And once she gets off the plane, Sam who was in the airport to see someone off, sees her and can't keep his eyes off her and tries to follow her but couldn't catch her. Jonah who has been going through the mail that his father has gotten ever since he was on the radio, sees the letter Annie wrote on a whim but didn't send it but her friend did. He tells his father this could be it. But Sam doesn't think he could have a relationship with someone who lives so far away.