While it pains me so, I must admit that upon recent rewatch of You’ve Got Mail this past year, I was struck by its many problematic aspects. Despite its place in the pantheon of romantic comedies from a bygone era, the film is starting to show its age as a paragon of romantic story telling, wrinkles and all.

The issues mostly begin and end with its very flawed and problematic characters. Now, I can go after Joe and Kathleen for emotionally cheating on their significant others. Or I can skewer Joe’s ignoble character where he essentially manipulates Kathleen into falling in love with him. I can go so far as to call Joe a sociopath – his taunting and prodding of Kathleen in the scene where he stands her up (unbeknownst to her) borders on sadism. But 25 years on, all of that is well worn territory.

As much as I hate to pick on Kathleen, who is already the emotional punching bag of the film, I have to indite the film for her characterization. Kathleen is a frustratingly docile in nearly every aspect of her life. It’s excusable in some respects, where she is a victim of harsh capitalistic realities that lead her to close her beloved store. In other situations, however, the film robs her of the ability to pro-actively choose and alter her circumstances. She isn’t even given the dignity to end her tepid relationship with Greg Kinnear; he hijacks the conversation to break up with her first as she sighs a breath of relief.

Things just seem to happen to Kathleen or for her own good, whether with Greg Kinnear relieving her of a bad relationship or Tom Hanks manipulating her into a “good one” (?). In 1998, there was a certain charm around an adorable Meg Ryan bouncing around New York and being serendipitously thrust into situations. In 2023, it’s infantilizing to see a woman who lacks any agency, particularly in her romantic life. Above all, for a film about a woman trying to assert herself in the face of bullies, there’s a bittersweet irony around her effectively ending up with one.

While the former me thought the film had the perfect ending, I’m surprisingly open to a sequel that sees Kathleen truly find her voice and show some character development. Perhaps the perfect role for an aging Meg Ryan, wrinkles and all. Who knew that you can actually improve on perfection, it just takes 25 years and a little social progress.