History YMMV / YouveGotMail

** Joe's half-aunt Annabelle is well-remembered for some pretty cute and funny moments.
** Christina is well-liked for her matter-of-fact personality and having some of the film's better lines.
** Frank is well-liked by people who think that he's a better romantic lead than Joe, and that [[LuddWasRight some of his negative ideas about the rise of technology are spot on.]]

* HarsherInHindsight: A minor plot point is Joe's father and his taste for younger women, which usually leads to trouble. Years later, his actor Creator/DabneyColeman would play [[Series/BoardwalkEmpire another older man with a taste for younger women taken to a horrifying extreme, and leads to tragedy for everyone involved.]]

* UnintentionalPeriodPiece: 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 Creator/MegRyan's character running an independent bookstore that risks being put out of business by the corporate giant. Today, [[https://www.usnews.com/news/best-states/new-york/articles/2017-05-30/indie-bookstores-hold-steady-in-tough-retail-market the situation is flipped:]] those large bookstore chains are in freefall thanks mostly to the internet, while independent bookstores are thriving again.

* FunnyAneurysmMoment: Looking back at this film with all of the documentaries and knowledge about being careful with strangers online is very sobering. True, neither was putting any overtly personal info out there, but with modern knowledge of internet scams and predators the sheer casualness of meeting someone in a chat room and talking to them immediately feels weird.
** On the other hand, their relationship is pretty similar to how people whose relationships start online work. (With less romantic comedy moments of course.)
** The entire "scrappy independent bookstore vs. corporate mega-chain" conflict thanks to web retailers and e-books slowly making the concept of physical bookstores themselves obsolete. In other words, both Kathleen and Joe lost in the end, as this ''Website/TheOnion'' [[https://entertainment.theonion.com/fox-books-files-for-bankruptcy-1819575288#_ga=2.100261278.1857644656.1519111329-1259430155.1519111328 article]] satirically posits.
*** This [[https://www.cbsnews.com/news/small-bookstores-are-booming-after-nearly-being-wiped-out-small-business-saturday/ report]] discussing how small independent bookstores are making a ''[[{{Irony}} comeback]]''.
** The film was released by Warner Bros., with AOL being used by the main characters. Three years after the film's release, AOL and Time Warner merged, which became one of the biggest mistakes in corporate history and AOL would be spun off eight years later.

* TheyWastedAPerfectlyGoodPlot: 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 foamier competitor happens completely offscreen.

* RetroactiveRecognition: Creator/SaraRamirez as the cashier who's annoyed by Kathleen (and charmed by Joe).

* SoOkayItsAverage: The general consensus of the film.

** Christina is well-liked for her matter-of-fact personality and having some of the film's better lines. I

** Joe's half-aunt Annabelle and half-brother Matt are well-remembered for some pretty cute and funny moments.
** Christina is well-liked for her matter-of-fact personality and having some of the film's better lines. It also helps that she is played by Creator/ParkerPosey.

* SpiritualSuccessor:
** To ''Film/TheShopAroundTheCorner'', adapted from the same play but set in different time periods with different characters.
** To ''Film/SleeplessInSeattle'', which also starred Hanks and Ryan. Critics also noted the films' vaguely similar plots — in ''Sleepless in Seattle'' they don't properly meet until the end, while in this one, they meet right away but spend a good portion of the film apart or unaware that each is the other's online paramour. (See ThoseTwoActors on the [[Trivia/YouveGotMail Trivia]] page.)
** Arguably to 1957's ''Film/DeskSet''. Both are romances set in New York, feature a ThoseTwoActors couple (Creator/SpencerTracy and Creator/KatharineHepburn), involve conversations about technology and people at risk of losing their jobs to progress, and are written by at least one Ephron. [[note]] ''Desk Set'' was adapted for the screen by Henry and Phoebe Ephron, Nora Ephron's parents.[[/note]]

* WhyWouldAnyoneTakeHimBack: 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.
** Debatably, she probably wouldn't have, if not for the [[TheRevealPromptsRomance reveal of Joe as NY152]], whom Kathleen knew and cared for before Fox Books even opened.

* IdiotPlot: {{Averted}}. As Creator/RogerEbert points out, just when it seems that "a word from either party would end the confusion," the film throws a curveball by allowing Joe Fox to figure out Kathleen's identity, which presents a whole new set of confusions.

** Christina is well-liked for her matter-of-fact personality and having some of the film's better lines.

* JerkassWoobie: 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. 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.

* JerkassWoobie: Joe has his jerkass moments for sure, but he always regrets them afterwards, too late to do anything about it. Considering the selfish, 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 sensitive as he is. 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.

* JerkassWoobie: Joe has his jerkass moments for sure, but he always regrets them afterwards, too late to do anything about it. Considering the selfish, 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 sensitive as he is. In the final scene in particular, he approaches Kathleen cautiously, unsure if his efforts to redeem himself have been enough for her to accept him as NY152 and thinking he's hurt her again.

** To ''Film/SleeplessInSeattle'', which also starred Hanks and Ryan critics noted had a vaguely similar plots — in the first film, they don't even meet until the end while in this one, they meet right away but spend a good portion of the film unaware that each is the other's online paramour. (See ThoseTwoActors on the [[Trivia/YouveGotMail Trivia]] page.)
** Arguably to 1957's ''Film/DeskSet''. Both are romances set in New York, feature a ThoseTwoActors couple (Creator/SpencerTracy and Creator/KatherineHepburn), involve conversations about technology and people at risk of losing their jobs to progress, and are written by at least one Ephron. [[note]] ''Desk Set'' was adapted for the screen by Henry and Phoebe Ephron, Nora Ephron's parents.[[/note]]

** To''Film/TheShopAroundTheCorner'', adapted from the same play but set in different time periods with different characters.

* SpiritualSuccessor: Arguably to 1957's ''Film/DeskSet''. Both are romances set in New York, feature a ThoseTwoActors couple (Creator/SpencerTracy and Creator/KatherineHepburn), involve conversations about technology and people at risk of losing their jobs to progress, and are written by at least one Ephron. [[note]] ''Desk Set'' was adapted for the screen by Henry and Phoebe Ephron, Nora Ephron's parents.[[/note]]

* SpiritualSuccessor: Arguably to 1957's ''Film/DeskSet''. Both are romances set in New York, feature a ThoseTwoActors couple (Creator/SpencerTracy and Creator/KatherineHepburn), involve conversations about technology and people at risk of losing their jobs to progress, and are written by at least one Ephron (Nora Ephron's parents, Henry and Phoebe, adapted the play for the screen).