Sam Baldwin (Tom Hanks) is an architect in Chicago who lost his wife, Maggie, to cancer 18 months back. He now lives in Seattle with his young son, Jonah (Ross Malinger), who persuades him to go on the air and discuss how much he misses Maggie with the hope that his story will touch listeners, and they’ll seek him out so he can find a new wife (since he’s too forlorn to do so himself).
One of the listeners is Annie Reed (Meg Ryan), a reporter for The Baltimore Sun. She’s engaged to Walter (Bill Pullman) but realizes her relationship is missing that special spark when she finds herself weeping during a showing of the classic 1957 film An Affair to Remember, which she attends with her pal, Becky (Rosie O'Donnell). Annie writes a letter to send to Sam saying that the two should meet atop the Empire State Building on Valentine’s Day (as in An Affair to Remember), but isn’t up to sending it. Becky, good pal that she is, takes the initiative and mails the letter out on Annie’s behalf. Of all the hundreds of letters Sam receives, Jonah is most taken by Annie’s and is convinced he should take a leap of faith and meet her in New York. Here’s a great scene of Jonah vetting the letters for Sam.
Jonah’s new pal, Jessica (Gaby Hoffman), persuades him to reply to Annie and agree on the meeting in New York. Here’s a funny, incredibly cute scene of the two idealistic go-getters plotting before being interrupted by Sam.
Sam begins dating the annoying Victoria (Barbara Garrick), whom Jonah despises, so he tries to sabotage their relationship—including this very awkward date.
Jonah catches Sam kissing Victoria and phones in to the radio station to ask for advice. Becky is tuning in and informs Annie, who can’t wait to get the 411 on the man she’s taken with, but she’s in bed with her boring fiancé, Walter, so she hides in a closet.
While dropping off Victoria at the airport, Sam spots Annie and immediately finds himself drawn to this beautiful woman, but he has no idea who she is.
Annie then sees Sam on the beach playing with Jonah but mistakes Sam’s friend for his girlfriend. “All I could say was hello,” she later tells Becky, repeating a classic line in An Affair to Remember.
Sam discusses An Affair to Remember with pals Suzy (Hanks’s real-life wife, Rita Wilson) and Greg (Victor Garber), but doesn’t find the storyline romantic, saying, “That’s a chick’s movie!” Meanwhile, he extols the romantic virtues of The Dirty Dozen. It’s a great example of screenwriter Nora Ephron’s gift for gab.
Jonah argues with Sam over his burgeoning relationship with Victoria and tries to persuade him to go to New York and meet Annie, who, he’s convinced, is the one destined to be with his dad.
After Jonah flies to New York on his own in search of Annie, Sam goes after him and finally finds him on the observation deck of the Empire State Building, where he’s been asking any and every stranger if they’re Annie. Meanwhile, Annie ends things with Walter at the Rainbow Room and rushes to the Empire State Building to meet Sam. And then, well, cue the fireworks (and waterworks).