At the time it came out, WHMS was a big hit, but critics compared it unfavorably to "Annie Hall". IMO Annie Hall has dated, and the Woody Allen character's self-absorption really stands out. Actually, both leads are pretty self-absorbed.
I think Harry and Sally flows better, as said above. They treat each other well, even when they're just friends, or even when they have a fight. For example, the day they helped their friends move in and Harry started having a meltdown over having run into Helen, and he and Sally end up outside fighting. But after she finishes he says "Are you finished?" and she says "Yes" and he says "May I say something?" and she says "Yes." and he says "I'm sorry." The movie is very real and heartfelt that way. It's very balanced. I trust the couple in this movie, and I think they are real friends who put each other's interests ahead of their own. Definitely holds up, and reflects a NYC that didn't vanish all THAT long ago, at least for that white, yuppie demographic. I also liked how after they slept together and they call their friends, their friends are like "Thank God!" you know that's realistic - you know all their friends were wondering why these two hadn't figured it out yet. Just a very good couple in this film. Usually I'd wonder why a woman as attractive as Meg Ryan was interested in Billy Crystal, but he's attractive in this film, and they just fit together.
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