Baldwin had lost his soul mate in Maggie and the loss of her has really hit him hard. One night, Jonah calls into a late-night radio station and talks about his dad's predicament and how he wishes that his dad would get back out there. Then, he forces his dad to talk about his loss and his feelings over the airwaves.
The radio host nicknames him Sleepless in Seattle and women all over the world fall for him over his story, including Annie Reed (Meg Ryan).
Reed lives in Baltimore and is engaged to Walter (Bill Pullman). Walter is quite possibly the nicest man in the world, though he suffers from about every allergy known to man. Although she is comfortable with Walter, Annie feels there just may be something missing. And, she writes a letter to Sleepless in Seattle.
The letter, however, was not mailed by Annie. Her friend, Becky (Rosie O'Donnell) mails the letter without her knowing. But, Annie continues to be what I can only classify as a stalker. She hires a P.I. to take pictures of Baldwin, and she herself even travels to Seattle and tries to track him down.
After discovering him and thinking he has moves on with another woman, Annie heads back to Baltimore and tries to move on with Walter. In her letter, though, she had mentioned that on Valentine's Day she would meet Baldwin on the top of the Empire State Building.
Not liking his father's current girlfriend, Jonah has become infatuated with Annie after reading her letter. He begs his father to go to NYC for Valentine's Day to meet her - but Baldwin refuses. Jonah's friend, Jessica (Gabby Hoffman), breaks into her mother's computer (her mother is a travel agent) and books Jonah on a flight to NYC.
I found it pretty darn fascinating that a movie that stars Meg Ryan and Tom Hanks, and the two of them are in pretty much two scenes together throughout the entire film. There is a small scene (which is basically two scenes) where he sees her at the airport, and then they see each other when she is stalking him. Then, at the conclusion of the film - and that's it.
The movie to me was, adequate. I don't really think this movie was made for me. I love Hanks and Ryan is cute - and I can take a love story or girly movie with the best of them, but even this one was far too sappy for me. But, it totally worked for a lot of people and it is brought up as one of the greatest love story movies whenever those are talked about. So, for some people it works - and it setup one of Hanks' other films which I will talk about shortly.