I love a good 2000's romcom (except When Harry Met Sally—fight me). However, I have a bone to pick with almost all of them. Jenna Rink's wildly extravagant apartment on a magazine editor's salary? Get out of town. She's the Man...just...everything. While You Were Sleeping? Kinda creepy. But I think that You've Got Mail takes the cake, despite it also being one of my favorite romcoms of all time. (And the reason I subjected myself to The Godfather.)
I'm Obsessed With 'You've Got Mail'—Minus This Enormously Problematic Plot Point
He did not!!!
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Published Feb 13, 2026
IMDb
The premise hooked me from the start. Neighborhood bookseller Kathleen Kelly takes on an Amazon-esque mega-bookstore run by the arrogant Joe Fox. Joe is hellbent on running Kathleen out of business. All the while, the duo are anonymous penpals on AOL (such were the days), exchanging messages as NY152 and Shopgirl. Both are seeing other people. (Does this count as cheating? You be the judge...) They never talk about their personal lives in the chat room. You'd think that they were destined to never meet. But eventually, Joe figures it out. And what's more, he falls in love with her. Which is a problem, because he's also trying to engineer the demise of Kathleen's family bookstore.
IMDb
That, however, isn't even the most problematic issue of the plot. It's that in the end, when Shopgirl and NY152 finally reveal their identities in the rose garden on Riverside Drive, Kathleen confesses that she was hoping that it would be Joe. They kiss—and there's not a word about the fact that he's just nuked her mother's beloved bookshop. That he's just destroyed her livelihood. And that in the lead up to the grand reveal, he'd been catfishing Kathleen, trying to bring her around in person while also continuing to court her anonymously as NY152. I mean, if I were Kathleen, I wouldn't have kissed him. Not before I'd thoroughly yelled at him, at the very least. The easy forgiveness had me scratching my head. Because if I recall correctly, I don't think he apologizes for the atrocity. And Kathleen, honey, why weren't you demanding one? There needed to be some form of major confrontation for everything else to feel right.
But who am I to judge? I don't know how I feel about Joe, but I do know that I'm due for a You've Got Mail re-watch.
