First off to answer the question everyone seems to have, Class of '09 and Class of '09 - The Re-Up are two different games. The Re-Up isn't a remaster, nor is it a sequel in the strict sense. It's more like an expansion. The first game starts you at the beginning of Nicole's second year of high school and some story routes continue all the way until graduation, others do not. The Re-Up story routes start at the beginning of Nicole's third year.
TL;DR You're supposed to play both games, not one or the other.
Anywho, I decided to play Class of '09 on a lark and didn't turn it off until I'd gotten every ending and taken every story route. To be fair, it only took 5 hours and I've seen people say they've done it in 3. Right from the first choice they give you I was hooked. TBH, the game is really funny, which probably says more about me that I would like. I think to call the humour irreverent might be putting it mildly.
But one thing that did bug me just a little was the tonal shift between the original game and the Re-Up. Specifically with Nicole and Jecka's characters. The first game starts with Nicole telling you she's a sociopath. And for the first game she is largely apathetic to everything around her. She really doesn't care about anything going on around her, or how her actions affect others. But you never get the feeling that she's acting maliciously; it seems more like she's trying to find a way to feel SOMETHING, anything at all. But in the Re-Up, she is very much acting maliciously. She will go out of her way to make others miserable. It's even brought up on a couple routes where she's called out for putting in way, way more effort to get back at a teacher for assigning her work than it would for her to just do the work that was assigned. I mean, maybe this is in character for her? Maybe they only time she feels anything is when she's being a heinous bitch?
Jecka changes a lot between the two games too. In the first game I got the impression she's kind of on the same level as Nicole when it comes to school. She complains about having to go to class, but usually goes along with Nicole with very little persuasion. That's actually pretty much her character in the first game - points out that what Nicole is planning to do is dumb/bad/pointless, then inevitably going along with her anyway with virtually no convincing. In the Re-Up, you see she's actually kind of a serious student. When she tells Nicole she has to go to class she… goes to class. She's planning on going to college, and knows she can't behave like Nicole if she wants to get there. This change in her personality extends to how she deals with Nicole's schemes too. When Nicole crosses a line, she nopes out no matter how much Nicole begs. Again, this might be in character. She may have realized that Nicole is a bad influence on her and taken steps to get back on track.
Also, between the two games the girls went from casual recreational drug use to having a serious drug problem. In fact almost all the student seem to have a serious drug problem in the Re-Up.
I'm also a little sad that they never played into the Miss Lynn x Nicole's Mom thing a bit more. It didn't even spawn any fan art! But, it could work, right? I got the impression that Nicole didn't have anything against Miss Lynn personally - she actually seems to think Miss Lynn is hot - but rather resents her position of authority. And it's the position she resents, not the person in it; there even seemed to be a bit of begrudging respect there. Outside the school setting you'd think they'd get along.
PS. There are two different possible scenes at the start of the Re-Up. Either Nicole just shows up at school and talks to Jecka, or Nicole is in the girls' change room trying to tie a rope to hang herself with. Which scene you get is random (but I think the hanging one is rarer?), so just exit and restart until you get the one you want.
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