A few complaints...

Rating: Null/10 (14 August 2009)

-the tonality is a bit awkward. The comedy, even the 'highbrow' stuff, is really, really silly, and while that's not a problem at all, that the next scene is supposed to have a strong dramatic impact on the audience comes across as jarring and not in a good way because the transition is so clumsily handled much of the time.
-the movie thinks it has more gravity than it does. The Henry Miller quote ("the best way to get over a woman is to turn her into literature") explains this to me. Clearly that's what the screenwriters have done with their past relationships, but as a result, as I suspect such an attempt by most writers including myself would, the movie attaches a little too much gravity to what is really another office-born half-romance. The movie treats the subject matter with a sense of irony and there are scenes which plainly show the reality of the matter, but I really found it hard to care that much when watching it again. They never seemed all that compatible. They had just met and had some fun times. Tom got too attached. Why Tom's obsession should make for earth-shattering drama I don't understand. I couldn't help but think about the relationship I'm in and think how trivial this 500 days of events seemed next to the years invested mutually in a friendship then romance, the incredibly tumultuous events we've weathered together. Then I think back to "Annie Hall" and recognize that relative to my experience, that relationship can be seen as trivial as well. That I can, for the length of "Annie Hall", feel like that relationship is the summation of humanity's history of existence, says something about the quality of execution in that movie relative to this. The awkward dramatics (I RLY HOPE U R HAPPY SUMMAR, and the godawful Big Speech about how bad greeting cards are, wow, writers, feel good about writing what millions of bitter anti-mainstream sorts are talking about at this very moment... I've never heard that before!) and cheesy narration don't really help much at all, and betray at times the superb performances from basically all the actors in the film, but especially Gordon-Levitt. Even "Adventureland" from earlier this year, with its summer fling at an amusement park, feels more important somehow than this portrayal of half a billion corporate office 'romances' going on right now, maybe because it's predicated on the smoldering sexual energy of the leads instead of attempting to deal (and clumsily) with stuff like fate and true love and that.
-the characters really, really are lacking in depth. Summer can be read as an interesting subversion of the manic pixie dream girl character, but Tom is a cultured version of a sitcom character and everyone else in the movie a caricature. The screenwriters appear to be cultured themselves, but only manage to loan this characteristic to their characters on a temporary basis, turning them right back into regular, plain, dull corporate annoyances who shop at IKEA (but go to cool-looking record stores and to see The Graduate!) in a matter of seconds. They're all too reminiscent of people I meet every day with the pretense of cultural interest and all the snobbery attached to it (including instant dismissal of sports culture, to my great annoyance), but very little actual knowledge of anything beyond the absolute mainstream of the underground (Smiths and Bergman references galore, but try talking to them about The Trash Can Sinatras or Jacques Rivette).
-that final scene. Oh god, that final scene. Oh god, that final scene.
All that said, I still liked it, just because it's a tremendous, very quotable comedy and genuinely clever at times, unlike Juno and such, and has some great movie scenes like the split-screen one and the musical montage and what follows, the art movie/Bergman parody/homage etc. etc. The comedy's great, too bad the drama's so clumsy.