Every male-centric movie (basically every movie) has a love interest, I don't know why, but it does. They try jazzing it up by making the female lead QUIRKY or SPECIAL, but they just suck.
Every socially awkward guy in the world fucking loves her and every "unique" girl wants to be her. They should stop. Not only is Ramona Flowers not a loveable character; she's not even a good character. Granted, this world is supposed to be full of flawed, aimless twenty-somethings, but her dysfunction is entirely defined by inconsequential quirkiness like dying her hair and rollerskating, but doesn't actually have any depth to warrant her flakiness, irresponsibility, and that whole part about forcing a guy she doesn't even seem that interested in to battle all of her exes. That's a completely dick move, and Scott Pilgrim is a real wiener for going along with it. Kim Pine 4 Life.
Zack Morris' love for Kelly Kapowski was one of the driving forces of the entire series, and it never made any goddamn sense. Her character is a prime example of someone we were just supposed to be on board with loving for many years entirely because she was pretty. Prettiness can maybe buy you a year of believable infatuation, but beyond that, you really need some kind of personality. And Kelly didn't have one of those. She was just a generic popular girl who never even laughed at Zack's antics. Jessie Spano, on the other hand, now there's a girl to get excited about.
Billy Murray spends lifetimes reliving the same day in this movie, and, by the end he's learned compassion and the ability to appreciate life and those around him. That's all very good, but, this otherwise perfect movie has one big flaw: Andie MacDowell. The pursuit of Andie MacDowell becomes the focus around which Bill Murray improves himself, which makes it really annoying that her character sucks so much. Her personality is gratingly earnest and dull--she always toasts to "world peace," ugh--and she's completely won over by cheesy bullshit, like ordering the same gross cocktail and that whole thing with the ice sculpture of her face, which any normal person would find creepy. There's no way a man who has experienced near infinite days would be satisfied by someone so bland. Then again, there's probably no way he could possibly live a satisfying life once the passage of time started up again. This kind of thing will really fuck you up.
You might argue that this entire movie is incredibly stupid, and therefore, there's no point in nitpicking the details. Well, you're only half right. The movie IS majorly idiotic, but it also has a ton of funny characters and enjoyable plot lines, so it's worth highlighting the fact that the main plot line, our protagonist's life-long pursuit of this "amazing" girl, is complete shit because the object of his desire is a total blando. It's not even possible to criticize her character on a more detailed scale because there is just nothing to her. Half of her screen time is her sulking on a couch. When the movie came out, the producers must have thought that Jennifer Love Hewitt was enough of a star that there didn't need to be an qualifying characteristics necessary for the audience to love her as much as Ethan Embry did. But that Jennifer-Love-Hewitt-fan-club ship has sailed. If you watch this movie again, just fast-forward to the parts with Seth Green and Claire, from Six Feet Under.
Katherine Heigl is the Andie MacDowell of the 21st century. We're supposed to be happy for Seth Rogen's character at the end of the movie because he has this lovely little family and a newfound life purpose. But we can't be happy because fucking Katherine Heigl is the worst. This is actually a situation where the character probably wouldn't be so bad in another actress' hands, but she takes ambition and a no-nonsense attitude and turns it into nagging, fun-killing, don't-do-drugs-with-Paul-Rudd awfulness. I'm sure that Judd Apatow would agree with me when I say that, if time travel were invented, but the catch was that it could only be used for one purpose in the entire universe, it should be used to recast movies that stupidly cast charmless insufferable actors like Katherine Heigl.
Jenny is supposed to be a fickle, uneven character that embodies the social change happening in Forrest's lifetime. Ok. But that doesn't mean she's forgiven for always stringing him along and ditching him, then keeping his child a secret until she's dying. That's not the kind of girl you want your main character to end up with. Also, you know, that whole bit about the questionable ethics of making sexual advances towards a mentally impaired man. We can all agree that that's pretty messed up, right?
You know you're a shitty character when Shannen Doherty seems more appealing than you do. In fairness to Claire Forlani, Kevin Smith always writes terrible female characters, so it's not all her fault, but that bad cover-up of a British accent sure didn't help her seem like a less whiney, obnoxious, unloving jerk. She breaks up with a her boyfriend because he's upset that she canceled the trip where he was planning to propose, in order to let her dad set her up with other guys. Also, her dad is way too much of a dick to think about marrying into that family. The next Thanksgiving after the events of this movie must have been a shitshow.
Rule 1: don't fall in love with any woman who cheats on her fiancé with you. Rule 2: don't put Andie MacDowell in movies.