* {{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.
* SugarWiki/AwesomeMusic: The film's closing credits song, "[[https://www.youtube.com/watch?v=hn4pvXY-pYQ Anyone At All]]", was written and sung by the legendary singer-songwriter Music/CaroleKing, and is exactly as good as you would expect from an artist of that caliber.
* EnsembleDarkhorse:
** Joe's half-aunt Annabelle is well-remembered for some pretty cute and funny moments despite getting very few scenes.
** Christina is mostly a SatelliteCharacter but is well-liked for her matter-of-fact personality and having some of the film's better lines.
** DisposableLoveInterest 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.]]
** Patricia has a larger fanbase than the size of her role and her amount of screen time might imply due to Creator/ParkerPosey giving her plenty of hammy moments and the occasional bit of HiddenDepths.
* GeniusBonus: 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.
* 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, leading to tragedy for everyone involved.]]
* HilariousInHindsight:
** Tom Hanks telling [[Film/CatchMeIfYouCan a Knock Knock joke.]]
** Kathleen becomes confused when Joe explains [[TangledFamilyTree that Matt and Annabelle are his half-brother and aunt respectively]] due to his father and grandfather both dating younger women. [[Series/ModernFamily Wonder why that sounds so familiar a decade later?]]
* 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, 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.
* RetroactiveRecognition: Creator/SaraRamirez as the cashier who's annoyed by Kathleen (and charmed by Joe). Creator/ChrisMessina as a Fox books employee who doesn’t know the difference between the books ''Ballet Shoes'' and ''Skating Shoes''.
* RonTheDeathEater: Joe is written as a flawed yet decent man who goes through some CharacterDevelopment and introspection. A fair number of fans view him as a complete BitchInSheepsClothing 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.
* TearJerker: 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 [[LampshadeHanging 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 [[StarCrossedLovers 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.
* 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 former competitor happens completely offscreen.
** A number of subplots were initially planned for the minor characters, but were cut from the final film. See DeletedScene on the Trivia page.
* 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. In the mid-2010s, [[https://www.usnews.com/news/best-states/new-york/articles/2017-05-30/indie-bookstores-hold-steady-in-tough-retail-market 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.
* 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.