Since I'm not now, nor ever been married, it's always fun to watch budding relationships and misunderstandings in a romantic comedy and add the holidays into the mix, it's a whole bunch of fun!
Starting with the relationship of Annie Reed (Meg Ryan) and Walter (Bill Pullman) the two are spending Christmas with both sets of parents and they announce their engagement at Annie's parents house during dinner.
From the get go, you can see the hesitation in Annie as she tries on her grandmother's dress in the attic and it rips. She knows its a sign and begins to doubt her relationship with Walter.
As each drive separately to Walter's family, Annie fumbles around with the radio and stumbles across a radio call in show, hosted by Dr. Marcia Fieldstone (the voice of Caroline Aaron). Annie thinks the callers are crazy until she hears a young boy call in by the name of Jonah Baldwin (Ross Malinger).
She (and the other listeners) are generally caught up in his call since he just wants his dad, Sam (Tom Hanks) to be happy since the death of his mother a year or so before.
Sam hears Jonah on the radio and after yelling at him, he starts to open up to Dr. Fieldstone and Annie finds herself getting more caught up in the conversation.
She stops at a diner and everyone is listening to the show while the waitresses are giving their two cents about how they'd like to meet Sam, but unfortunately, he's in Seattle.
The New Year comes and goes and while at a party, Walter suggests to Annie that the two spend Valentine's Day in New York since he has some business to attend to and she agrees.
Back at work, Annie, a reporter, goes into her editor Becky's (Rosie O'Donnell) office where she asks her if she had heard the radio show. Becky tells her that she hadn't and while not coming out and saying anything, she hints to her that maybe she should do a feature on call in radio shows.
Becky doesn't think there's much of a story in it, but after the call is replayed as a "Best of Dr. Marcia Fieldstone" Becky calls Annie in the middle of the night and tells her that the kid is on the radio again. This time, Becky slyly gives her the okay to do a story, because now she's hooked.
In Seattle, Sam's friend Jay (Rob Reiner) tells him that he should start dating again and thinks that one of the designers Victoria (Barbara Garrick) would be a good match for him. Reluctantly, Sam asks her out.
Across the country, Annie and Becky are trying to compose a letter to Sam, known only as Sleepless in Seattle and while still questioning her love for Walter decides that it's a bad idea and throws away the letter, which Becky lifts and sends anyway.
Annie continues to plan the wedding, while Jonah and Sam receive a ton of mail from the show. They go through some of the letters and Sam realizes that these women are crazy and forgets decides to ignore them.
A few days later, Annie's letter arrives and after Jonah reads it, he knows that this is the woman for Sam, but he throws it away after telling him that she's clear across the country.
Jonah responds back to Annie, with the help of his friend Jessica (Gaby Hoffmann) and after obsessing over Sam and Jonah, Annie decides to go to Seattle "just to see what they look like." Becky's on board and tells her that the paper will pick up the tab.
Annie hires a private detective and with address in hand, heads to Seattle, but when she gets there, she sees a woman (Rita Wilson) run and hug Sam and Jonah. Annie thinks that it's the woman from a picture taken at a restaurant since it's just the back of her head.
After hearing Suzy tell Sam and Greg (Victor Garber) the plot of An Affair to Remember Jonah sends a letter to Annie and asks her to meet him at the Empire State Building on Valentine's Day.
When Jonah meets Victoria, he instantly hates her and once he sees the two kiss in the kitchen, he calls Dr. Fieldstone again panicking about how Sam was kidnapped by a 'ho.
Sam is furious with Jonah and grounds him, so with the help of Jessica, Jonah heads east to meet Annie, with or without Sam.
Over a romantic dinner, Annie keeps staring out at the heart on the Empire State Building and she tells him that she's in love with another man, but she's never met him. She tells him that she's not in love with him and he tells her to go to the Empire State Building to see if he showed up.
Annie hurries to the building, while Sam frantically looks for Jonah and promises to eventually kill him because of the stupid stunt he pulled and the two leave.
You could say that this is an updated version of An Affair to Remember with the Empire State Building as the backdrop, but you have to ask yourself too, can something like this really happen when it comes to love?