This is a decent movie with a good cast. I actually prefer this movie to Sleepless in Seattle; I think it's funnier and has the advantage of Hanks and Ryan actually sharing the screen together for more than the last 5 minutes.

The biggest problem with this movie is that it fails to stick the landing. There seems to be some commentary on big corporations driving mom-and-pop shops out of business. However, the film ends with the big corporation winning and Meg Ryan being left jobless. That seems like a weird way to end a movie but what do I know? I was expecting this movie to end with Hanks purchasing her store and gifting it back to her, or possibly closing his competing megastore. It's very odd that corporate greed wins out here and the script writers just kind of shrugged their shoulders.

There's also the questionable nature of their relationship once Hanks figures out the identity of his pen pal. I don't think most women would find it very romantic if a man they hated tried to woo them over the internet using an online alias. I'm not sure who made that decision, but for this movie to work like it was intended they should have learned about each other's identities at the same time.

You've Got Mail represents the tail end of the golden era of romantic comedies, during which writers and directors were trying to get an angle that would work for a more cynical movie-going public. Nora Ephron, with her rapier wit which she often hid within a cinematographic soft glove, was one of the more successful filmmakers of the later period. This film is a remake of The Shop Around the Corner from an earlier rom com era, so there are layers to the references in this movie, and if you catch them all, some of them are quite ironic. Especially the unintended ones, though. The script updates the story of the big retailer putting the small retailer out of business even as the two proprietors fall in love by recasting the retail stores as bookstores (this was actually a very big deal in the 90s) and the pen pals are corresponding via email rather than snail mail this time around. Looking at this film all these years later, you can't help but marvel at the fact that the filmmakers had written a romance about a big box bookseller winning the girl by utilizing a tool that was destined to put him out of business one day. Tom Hanks and Meg Ryan both have a great deal of personal charm individually and solid chemistry together, so the movie works on that level. Some aspects of the film aged less well than others. For example, the opening scenes that show Hanks and Ryan seeing their lovers off to start their days, and then sneaking back to their laptops to emote at each other via email, are played as cute hijinks, when today their actions would be recognized as an emotional affair. It's immediately clear that neither one is involved with a suitable lover, and then those lovers very conveniently (and somewhat ironically) develop a connection with each other, but still. This movie is somewhat of a time capsule, and still worth a watch with that in mind. Hanks and Ryan do a better job of selling the idea that these two can overcome his rampant trampling on her livelihood through their personal connection to each other much more successfully than the script manages to do.