Are we supposed to believe that Cassidy is more attractive than Aimee?

I think it's really accurate. Aimee is super nice, but she's also not as friendly as Cassidy and she's more interested in reading and helping her mom out. And when Aimee went to the party, Sutter noted that a couple of guys were flirting with her. It's more of who put themselves out there more by going to parties and talking to guys.

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Guys started hitting on AIMEE the moment she arrived at the party. I don't know if she's shy because she was rejected or she was rejected for being shy, but it's or the other. She's not a nerd, but that doesn't mean she has to be interested in hanging out with other people.

Also, she doesn't wear a lot (or any) make-up. Look at the fancy dress CASSIDY wears at the party where SUTTER catches her with MARCUS. And in the outside party, she's wearing a semi-open shirt.

It seemed to me that at the beginning they made Aimee look, while not unattractive, not exactly attractive either. She was not wearing makeup, she had her hair up/back, and her clothes were nothing special. Contrast that with the prom where she was made up, her hair really did look thick, and that dress really showed off her slim figure and long legs. They were going for a transformation.

Add to all that, that Cassidy was part of the "in" cool group as was Sutter, and Aimee clearly wasn't. So yes, for purposes of who is considered more of a catch, Cassidy is more attractive than Aimee, at least at the beginning.

Yeah, I thought about that too. I think that Shailene's character is supposed to be less attractive than she is in real life. Because honestly she definitely out does Cassidy in the looks department, in my opinion anyways.

You guys are analyzing this subject with way too much intensity. It's basic John Hughes 101 when it's comes to a movie characters perceived cuteness factor vs reality. Hell, Disney was tackling it back in the dark ages. Two great examples come from "Can't Buy Me Love" and "Not Another Teen Movie". In the first, the school's biggest nerd pays the most popular girl to pretend she's dating him, and in a day, he's practically the prom king. Then after they find out its a rouse, everyone turns on him.

The second offering, "Not Another Teen Movie" features a scene that parodies "She's All That", wherein the hunky high school QB is challenged by one of his cronies, to popularize the most hopeless charity case in the school. The joke comes from the fact that he chooses to look past a horrific crop of trolls and lepers, finally deciding upon a super gorgeous nerd, plagued only by "glasses", "a ponytail", and her choice of attire(overalls).

"The key is, you've got to be crazy to maintain your sanity"

You're pretty much on your own here, discounting all the people in the thread trying to find ways to say they preferred Aimee because it suits their young idealistic mindsets more.

I mean, I'm sure they preferred Aimee as a person, they might have preferred her as a girlfriend, but there is no "are we supposed to..." regarding which one was the more obvious 'hot girl'. Granted, the director could easily have created the reverse situation with clothes, make-up, style and attitude, but they didn't. They chose to have Cassidy as the hot girl and Aimee as the shy/nerd girl.

Let's just sum things up by a direct comparison. How many teenage boys do you think got a boner from that short sex scene with Cassidy in the beginning? And how many got one from the more down-to-earth-sex-scene of the first time Sutter and Aimee had sex?

That's right.

In high school popularity makes one sexier as well.