If you wanted to do a revisionist reading of You’ve Got Mail, you certainly could do that. You could focus on the skewed power dynamics between Kathleen and Joe—not just on the difference between the big-box behemoth and the mom-and-pop shop, but also on the even bigger differential here: The fact that Joe knows who Kathleen is, and the fact that the knowledge is not mutual. You could focus as well on the mixed messages about capitalism, or on the fact that people of color, in this love story—Dave Chappelle, in particular, as Joe’s friend and business associate—are treated primarily as props. You could focus on the fact that Kathleen’s cast-off boyfriend, Frank Navasky (Greg Kinnear), the Luddite-obsessed quasi-intellectual who loves Heidegger and typewriters, is in fact the most prescient character in the movie: He’s the only one here who seems rightly suspicious of the internet’s alleged wonders.
But there’s an even more glaring problem with the movie—another flaw that did not require the gimlet gaze of retrospect to make plain: the fundamental jerkiness of Joe Eff-Oh-Ex. The fact that he can be casually cruel. The fact that the plot of this particular rom-com involves him manipulating Kathleen and hoping—assuming—that she’ll eventually be grateful for the manipulation. (“I wanted it to be you,” she tells him when he finally reveals what he’d known all along; “I wanted it to be you so badly.” In a movie that makes Parker Posey seem like a villain and the fashion of the 1990s seem like a good idea, it’s the most unrealistic line of all.)
The film evades its own overarching problem primarily by insisting that its male lead is in fact—actually, underneath it all—a good guy. It makes this case by giving Joe an extremely adorable dog, and suggesting that he’s good with children (at least those he is related to), and assuming that telling knock-knock jokes to a weary grocery-store worker is the stuff of charm rather than smarm.
It makes its case, as well, in a more meta kind of way: Joe is played, of course, by Tom Hanks, and You’ve Got Mail invests a lot of faith in the idea that the characters Hanks has played in his previous pairings with Ryan—Joe (another Joe! a better Joe) in Joe Versus the Volcano, and Sam, the grieving single dad, in Sleepless in Seattle—have somehow transferred over to this other movie. Joe couldn’t be that bad of a guy, You’ve Got Mail suggests, because Joe, on some level, is the same person who met Meg Ryan at the top of the Empire State Building, his precocious son in tow, against Manhattan’s dreamy skyline.
But here is the film’s primary argument that Joe deserves Kathleen—Kathleen, who is smart and who is kind and who looks like Meg Ryan: Joe, it insists, simply can’t help his own jerkiness. He can’t be blamed for any of it, because he is a product of forces beyond his control. He’s a child of privilege, first of all, whose dad is the kind of guy who, when Joe tells him that he’s broken up with his live-in girlfriend, would respond, “Would I like her?” And he’s a capitalist who has convinced himself, as he puts out of business the store Kathleen owns—the one she inherited from her mother, the one she planned to pass on to her own daughter—that “it’s not personal; it’s business.”