I have seen You've Got Mail (1998) about five hundred times. I grew up on it, much as I grew up on numerous romantic comedies that don't have sex scenes. Since it was approved by my mother, my sisters and I watched it over and over again. We watched Kathleen Kelly (Meg Ryan) fight to keep her little bookshop open on the Upper West Side. We watched Joe Fox (Tom Hanks) threaten her livelihood with his Barnes & Noble stand-in, Fox Books. We watched them flirt online in a pre-aughts-unsullied Internet chat room without knowing each other's identity, and reveled in Kathleen's minor victories when she unwittingly used Joe's advice against him. There's never a question that they'll end up together, but seeing them overcome the unfortunate career situation is really enjoyable.
However, it's a wordy film. There is a lot of talking in "You've Got Mail". A lot of musing, a lot of literati references. There were a lot of scenes I tuned out of when I was younger. Watching it now, it's fun that I can understand the conversations that used to mean nothing to me. I appreciate the subtleties. (Especially Parker Posey. She's a gem.) Here, to get this out of my freaking system, is my favorite part of the movie that I discovered when I got big.
Kathleen's boyfriend, Frank (Greg Kinnear), is a journalist. He frequently and comically tortures himself with questions about time and things that have become obsolete. (His support for Kathleen's bookstore miiiiiiiight have been a clue that it wasn't going to survive.) In a scene where he talks over her, trying to support her, we learn Kathleen's greatest fear:
I always overlooked that line. The Lone Reed line overshadows it. But it's key to understanding Kathleen's struggles in the story. Hers is an understandable fear. Most people will look around at their careers or their jobs and wonder the same thing. Whether you enjoy your work like Kathleen or are doing it for the paycheck, we can't avoid taking stock of what we put our time and effort into. In this situation, Kathleen is being forced to examine her bookstore from the point of view of the conglomerate pushing her out. She inherited the store from her mother and so it has emotional significance for her, but if the going gets tough, is her work important enough for her to fight for it?
Later, Kathleen meets Joe at an industry party. The first time they met in her store, he kept his last name from her. When she figures out that he's part of Fox Books, she goes on a rampage, accusing him of spying on the competition. Joe knows he did her wrong. However, he's not one to admit that. He's about the bottom line and he wants his new venture to succeed. So instead of engaging in Kathleen's emotion, he remains passive and infuriatingly calm. But that comment about him trying to spy on her gets him enough to poke her back.
Joe was most likely trying to save face and shut her up: You think you're a threat? Nice try, lady. You're not. You're inconsequential. That word. It's devastating! Kathleen's deepest fear is that she's fighting for a cause that isn't worthy, that she herself is unworthy (which is probably why she comes off as the opposite, as virtuous). It's no accident that Joe knows exactly what to say to her. Indeed, it works, she's speechless, all she can do is point at him with a kitchen knife. And he knows it. He knows he cut her to the quick, as evidenced in his chat room confession later on. Here comes Mr. Nasty.
But: The feeling is mutual. Kathleen, while not as quick-witted as Joe in the moment, can be equally destructive. In the scene in the coffee shop when she's waiting to meet her Chat Room Prince Charming, Joe shows up and figures out that they've been chatting with each other all along. He doesn't reveal this information, however, and storms in without a plan or fully comprehending the situation. He doesn't understand how it's possible for two people to hate each other and be in love at the same time.
So he sits down and proceeds to torture Kathleen, making fun of the signals they had planned for identifying each other, teasing her that her man is never going to show up. He's lording it over her that she's probably at that very moment in love with him. But the fact of the matter is that he's in the same boat, he's just in denial. For now.
Finally, provoked beyond belief, Kathleen snaps at him.
It's that line about no one remembering him that wipes the smug smile off Joe's face. Kathleen, just about in tears, is busy in the throes of being able to speak her mind finally, but even that satisfaction is quickly thwarted when she realizes how much she hurt Joe's feelings. Turns out he has the same fears that she does. That no matter how many books he brings people, that no matter how much money he makes, that's not what matters.
It's such a terrible feeling, to speak your mind when you wish it - as Joe had previously warned Kathleen during one of their Internet chats. Kathleen is devastated once again, but it's because of her own actions this time. She can't even blame Joe for it, other than the fact that he provoked her.
Joe realizes that he is in love with her and begins a journey to make amends and ingratiate himself to her. He is able to accomplish this easily - because of his subterfuge as her chat room confidant, yes, but it's more than that. Kathleen and Joe see each other. It's an extraordinary power, to see someone. To understand why they do things and what they strive for. As enemies, they exploited this power to harm each other. As lovers, Joe uses that ability to woo Kathleen instead. He comes over to Kathleen's apartment when she's sick and realizes that he's still bringing out the worst in her. He stops her from insulting him in order to help her avoid that horrible feeling again.
It's an example of there being a fine line between love and hate. Both require deep understanding of the other person and that understanding can be both used and abused. In this case, the whole story supports the fact that these two people are meant to be together - as a good rom-com should - right down to the speech and motivation of the two main characters. (Is there a form/content argument in there? I could have sworn there was ...)