The Major Flaw of You’ve Got Mail

Twenty years later, the film is a reminder of the giddy hopes—and, through its leading man, the inevitable disappointments—of the early internet.

Joe, in the process of belittling Kathleen's shop, her livelihood, and everything she stands for (Warner Bros.)

You’ve Got Mail premiered, as a not-very-holiday-focused holiday movie, in late December 1998. It was a film that could only have emerged from its particular historical moment: a rom-com about two people, Kathleen Kelly (Meg Ryan) and Joe Fox (Tom Hanks), enemies in life, who find soulmate-level connection via the magic of the dial-up modem. “In life, they’re at odds,” the film’s trailer intones. “Online, they’re in love.”

In late 2018, with the benefit of 20 years’ worth of retrospect, you could read You’ve Got Mail as a hopeful treatise on the human-communing powers of the internet. Or as a subtle commentary on the all-consuming power of capitalism. Or as a feature-length piece of product placement for America Online. Or as an epic by another means: a hero’s journey full of ups and downs, whose true protagonist is Meg Ryan’s choppy bob. But you could also see You’ve Got Mail as something more basic: a rom-com that, in the end, doesn’t quite deserve to be. You could read it that way precisely because the person the film insists is the film’s romantic hero—Joe, the scion of the Fox family, and thus the partial owner of the big-box Fox Books, and thus the enemy of the independent-bookstore-owning Kathleen—is, objectively, kind of a jerk.

Here are some of the things that Joe “Eff-Oh-Ex” Fox does over the course of the film:

  • He lies to Kathleen. Repeatedly. Systematically. It starts with an unplanned trip to Kathleen’s almost aggressively charming children’s bookstore, the Shop Around the Corner: When Joe realizes that Kathleen is not only “enchanting,” but also the person he is about to put out of business, he does everything he can to keep her from realizing who he really is. He pays in cash. He shushes his young brother when the boy insists that every animal is spelled “Eff-Oh-Ex.”
  • Things escalate substantially from there. When Joe realizes that Kathleen is also “Shopgirl,” the person with whom he has been corresponding in an over-30s AOL chat room, he realizes this twist well before she does. And he uses that information against her, sometimes quite cruelly. When Kathleen is planning on meeting her own cyber-correspondent, NY152, for the first time in person—and when Joe, showing up for the date, puts the pieces together—he joins her at the cafe, mocking Kathleen and the whole setup she has put together, from her red rose to her copy of Pride and Prejudice. A kinder person, realizing at the very least that Kathleen would end the evening assuming that she had been stood up, might have done things a little differently; Joe Fox, however, You’ve Got Mail suggests, is not an especially kind person.
  • One way the movie makes that clear: Joe, over the course of the film, commits several petty acts of jerkiness. At a party, he swipes his spoon over a significant percentage of the caviar lining a large plate of egg salad (the foodstuff is molded into a massive ring, because the ’90s had their way with us all). He does so with an ease that suggests he is practiced in the arts of communal food-hogging. When Kathleen points out the selfishness—“That caviar is a garnish!” she admonishes—he scrapes his spoon further down the plate, taking a school’s worth of pricey fish eggs for himself.
  • When Kathleen accuses Joe of going to the Shop Around the Corner as a spy, he replies thusly, his voice dripping with sarcasm: “I have in my possession the super-duper secret printout of the sales figures of a book store so inconsequential yet full of its own virtue that I was immediately compelled to rush over there for fear that it’s going to put me out of business.” (Shopgirl, telling NY152 about that encounter, will refer to Joe as the person who “recently belittled my existence.”)
  • Kathleen, trying to avoid Joe at the grocery store (You’ve Got Mail also features extensive product placement for Zabar’s), ends up in a cash-only line. She has no cash. Joe, overhearing this, comes over, ostensibly, to help her … and achieves his goal by condescending to the register attendant, who is reluctant to let Kathleen pay with a credit card. Joe tells the worker, Rose (Sara Ramirez), a knock-knock joke. (“Orange you going to give us a break by zipping this credit card through the credit-card machine?”) He treats the other people in line similarly, asking their names and, given the time of year, making them wish each other a happy Thanksgiving. The film seems to find all this extremely charming: Joe, fighting for common civility, and all that. It is not. It is demeaning to all involved, including Joe himself.
  • When Joe “crashes” the blind date Kathleen had set up with NY152, she says to him, “Please leave. Please, please leave, I beg you.” He ignores her.
  • When Kathleen gets the flu, complete with a runny nose and a fever, and Joe (kindly!) comes to visit her, she is not terribly in the mood to have a guest over. “I would really appreciate it if you would just go away,” she tells him. He (unkindly) ignores her again.

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.”

Joe is someone, the film implies, who needs to be saved—by, specifically, Kathleen and her kindness. “Do you ever feel like you’ve become the worst possible version of yourself?” NY152 asks Shopgirl at a climactic moment of the movie. “That a Pandora’s box of all the secret, hateful parts—your arrogance, your spite, your condescension—has sprung open?” The line is meant to suggest that Joe’s jerkiness is not a fundamental element of his personality, but rather a tragic contingency. That if he were coupled with someone better for him, maybe he’d be better himself.

It’s a strangely fitting attitude for this rom-com of 1998 to adopt for itself: It belies, after all, a great faith in humanity. That guy, scraping up all the most expensive food at the party, leaving none for anyone else? He’ll probably come to regret his selfishness. The man who, when the woman says, “Please leave. Please, please leave, I beg you,” decides, instead, to stay? He probably has his reasons. The hero who spends months lying to the woman he loves, hoping and assuming that she’ll be grateful for the manipulation? He’s just being romantic.

You could definitely apply the worldview of 2018 to You’ve Got Mail and find it lacking; you also don’t really need to. Its problems are implicit. Even for the late 1990s, when the World Wide Web was barely a decade old and when people associated the internet more with human potential than with human tragedy, this rom-com had a notably sad vision of romance. Kathleen loses her shop, and her inheritance, and her livelihood. She is manipulated by the man who contributed to the loss. None of that matters, though, You’ve Got Mail says, because Shopgirl has also logged on to the internet and found herself, against all odds, a guy who seems to be nice.