Update: I knew this would happen eventually. I swear, I searched my archives as thoroughly as I could before writing this. (Okay, I just searched "Stiles" and nothing came up.) But I've actually done this one before, over two years ago. Enjoy how my style has evolved since then!
[it is SEATTLE]
Julia Stiles: I don't give a damn about my bad reputation, as you can tell from this Joan Jett song blasting from my socially-unacceptable car.
Alex Mack: I care! I care so much! I want to be popular!
Joseph Gordon-Levitt: Oh man. She's so hot.
David Krumholtz: Put her in your spank bank, man.* She can't date unless her sister does. It's like The Taming of the Shrew...but in high school! How wacky!
Joseph Gordon-Levitt: Wait! I know! We can get someone to pay someone to date her sister and then she can date me, because I am charming.
Generic Hot Dude: That would be me. I have money, and am stupid. Now I will draw a dick on your face to prove my alpha male status.
David Krumholtz: Okay.
Joseph Gordon-Levitt: Now, who is crazy enough to date the sister?
[they see Heath Ledger SMOKING in class and hear RUMORS about him KILLING people and EATING LIVE ANIMALS]
David Krumholtz: It's perfect! He's so surly and antisocial! And probably poor!
Generic Hot Dude: Here is some money. Please take out the sister of the girl I like.
Heath Ledger: Though I have literally no vested interest in your problem, and the amount of money you are giving me is negligible considering the amount of effort I will likely have to put into this ordeal, I accept your offer.
[he goes to a ROCK SHOW for a LOUD GIRL BAND to WIN her AFFECTIONS]
Julia Stiles: I hate you, I think.
[she RUNS into the Generic Hot Dude's car for FUN]
Generic Hot Dude: My social status! Nooooooo!
[there is a HUGE PARTY]
David Krumholtz: I'm thinking about getting a Tercel. Yeah, that's a Toyota.*
Julia Stiles: I am so bored by the rituals of adolescence. I will drink a lot to assuage my boredom.
[she dances on a TABLE to "HYPNOTIZE" and everyone is like WHAT]
Alex Mack: I think I like that Generic Hot Dude.
[he does something DOUCHEY, as that is his FUNCTION]
Alex Mack: Oh wait, no. He is lame.
Joseph Gordon-Levitt: Nice guy score!!
Heath Ledger: You are drunk. I will help you.
Julia Stiles: I reject your patriarchal value system!!
[she BARFS on him]
Julia Stiles: Thanks for helping me. Let's kiss.
[he REFUSES because he is a GENTLEMAN, but she thinks it is because he DOES NOT LIKE her]
Julia Stiles: Now I hate you!!
Heath Ledger: I must regain her favor!
[Heath Ledger sings "CAN'T TAKE MY EYES OFF OF YOU" with a goddamn MARCHING BAND as he PRANCES on the BLEACHERS]
Julia Stiles: He has won my heart back, though I have never expressed an interest in grand gestures, marching bands, or The Four Seasons. I will free him from detention by flashing the soccer coach.
Generic Hot Dude: You need to go to prom with the older sister so I can bone the younger one.
Heath Ledger: I am starting to have doubts about this plan and its long-term effectiveness, since I have begun to actually like the older sister, but your money is so convincing.
[he plays PAINTBALL and exchange INTIMACIES with Julia Stiles]
Heath Ledger: Go to prom with me, though neither of us will like it.
Julia Stiles: You are forcing your societal expectations on me! I reject them! And you!
Alex Mack: Why do you hate everyone so much?
Julia Stiles: I had sex with the Generic Hot Dude, and he turned out to be a dick, and now I am suspicious of everyone, always. Oh, and that whole thing about our mom deserting us didn't exactly help.
Alex Mack: Just let me make my own decisions!! God!! I'm going to change into a diaphanous gown and sit on the tire swing and just HATE YOUUUU!!
Julia Stiles: Perhaps I will go to prom...for her sake.
[they GO, and of course SHIT GOES DOWN and people get PUNCHED and secrets REVEALED]
Julia Stiles: Now I will read this poem I wrote about you in front of the whole class, because that is a thing that real high school students do.
Heath Ledger: I was a jerk, and to make up for it, I spent the money I got from that Generic Hot Dude on this Guitar for you.
Julia Stiles: Now I love you again, because you got me a guitar.
[LETTERS TO CLEO plays on the ROOF of their SCHOOL for some reason]
Note: Allison Janney is also in this movie, and she is GREAT, though she is in it for, like, a second. Cat!