YMMV / You've Got Mail

• Adorkable: Kathleen's moments of vulnerability, enthusiasm about internet chat rooms, and miming punching movements while planning to fight back against Joe's business are all adorable.
• Awesome Music: The film's closing credits song, "Anyone At All", was written and sung by the legendary singer-songwriter Carole King, and is exactly as good as you would expect from an artist of that caliber.
• Ensemble Dark Horse:
  • Joe's half-aunt Annabelle is well-remembered for some pretty cute and funny moments despite getting very few scenes.
  • Christina is mostly a Satellite Character but is well-liked for her matter-of-fact personality and having some of the film's better lines.
  • Disposable Love Interest Frank is well-liked by people who think that he's a better romantic lead than Joe and that some of his negative ideas about the rise of technology are spot on.
  • Patricia has a larger fanbase than the size of her role and her amount of screen time might imply due to Parker Posey giving her plenty of hammy moments and the occasional bit of Hidden Depths.
• Genius Bonus: Thanks in part to all the main characters being quite literate, the dialogue offhandedly contains references to Anthony Powell, Mrs. Patrick Campbell's literary affair with George Bernard Shaw, Generalissimo Franco, Julius and Ethel Rosenberg... and The Godfather, of course.
• Harsher in Hindsight: A minor plot point is Joe's father and his taste for younger women, which usually leads to trouble. Years later, his actor Dabney Coleman would play another older man with a taste for younger women taken to a horrifying extreme, leading to tragedy for everyone involved.
• Hilarious in Hindsight:
  • Tom Hanks telling a Knock Knock joke.
  • Kathleen becomes confused when Joe explains that Matt and Annabelle are his half-brother and aunt respectively due to his father and grandfather both dating younger women. Wonder why that sounds so familiar a decade later?
• Jerkass Woobie: Joe has his jerkass moments for sure, but he always regrets them afterwards, too late to do anything about it. Considering the egocentric, unstable family environment he grew up in (his father and grandfather remarrying multiple times and throwing Joe's inheritance down the drain each time), it's a miracle he is as decent and sensitive as he is, despite some moments of nastiness. In the final scene in particular, it's hard not to sympathize as he approaches Kathleen cautiously, first unsure if his efforts to redeem himself have been enough for her to accept him as NY152, and then thinking he's hurt her again as she starts crying.
• Retroactive Recognition: Sara Ramirez as the cashier who's annoyed by Kathleen (and charmed by Joe). Chris Messina as a Fox books employee who doesn’t know the difference between the books Ballet Shoes and Skating Shoes.
• Ron the Death Eater: Joe is written as a flawed yet decent man who goes through some Character Development and introspection. A fair number of fans view him as a complete Bitch in Sheep's Clothing who doesn't respect Kathleen for who she is, doesn't put enough effort into making his relationship with Patricia work, and takes driving his rivals out of business too far.
• Tear Jerker: Kathleen's last moments standing in her mother's book store, now an empty shell of its former self. The only thing she has left of it is its old-fashioned bell, and the memories of her mother.
  Sign on the door: "After 42 years, we are closing our doors. We have loved being part of your lives."
  • At some point near the end of the movie, Joe remarking on the tragedy that under different circumstances, had he not been Fox and she not been owner of the "Shop around the Corner", they could've been friends sooner instead of enemies. He tells her that if only she hadn't been hostile upon learning his identity, he would've meant to ask for her out on a date.
• They Wasted a Perfectly Good Plot: The last act of the film could have devoted a little time to Kathleen's employees adjusting to the shop's closure. Christina worries about whether she'd be able to another job earlier in the movie, but seems oddly calm when the shop does close, while George going to work for their former competitor happens completely offscreen.
  • A number of subplots were initially planned for the minor characters, but were cut from the final film. See Deleted Scene on the Trivia page.
• Unintentional Period Piece: The title alone immediately dates it to that period when America Online was America's largest ISP. It also centers around the booming expansion of big-box chain bookstores, with Meg Ryan's character running an independent bookstore that risks being put out of business by the corporate giant. In the mid-2010s, the situation had since flipped: those large bookstore chains are in freefall thanks mostly to the internet, while independent bookstores were thriving.
  • In the smartphone era, Kathleen and Joe's online relationship would have largely been through text messages. When they agreed to meet, instead of "I'll have a book and a flower", they would have traded selfies, and the second half of the film would be drastically different.
• Why Would Anyone Take Him Back?: Over the course of the movie, the closing of the bookshop causes Kathleen significant emotional pain, even going so far as for her to say it feels like her mother is dying all over again. Even if she found it within her to ultimately forgive Joe for his involvement in the store going under, it's still difficult to believe that Kathleen would happily have the daughter she wanted to leave her bookstore to with the man responsible for there no longer being a bookstore.