Wow! I can honestly say I did not expect such great feedback. I always thought I seemed like an amateur screenwriter.
So what you're saying basically is rework everything after pg. 5?
EDIT: I understand that it was a bit iffy to follow. But no, Will I is not gay, nor is he questioning his sexuality, and has no desire to be in Tiny's musical.
The book is just as slow-ish as the movie has started to be. I'll start reworking things though. i.e. putting in a GSA meeting, talking about Will's sexuality.
Also, you may have just read it wrong or I worded it wrong, but "Tiny Cooper." is just a word that'll be glimpsed by the camera. We'll see his hand actually
write out his name: "Will Grayson"
The only thing the audience knows is what they see on the screen. And as a reader, my job is to look past the written and imagine it on the screen. If I don't 'see' it, it didn't happen. If it's the impression I get, it's the impression the audience will get when seeing the movie. In the first 13 pages, there is nothing that shows us Will is gay or not. His complaints could be viewed as Tiny outing him, though the opening with Russ suggest he might already be gay. His comments about crying. These tiny pieces weigh in contrast to his words to Jane and Tiny about getting on with the ladies. If you want to emphasize that he's straight, have short sequence where he smiles at a group of girls walking past his locker that snicker and hurry off before Tiny and Jane approach. Unless sexuality is an important issue, don't dwell on it unduly. It becomes a lightning rod in the audience's mind.
I have to say my first impression from the letter is that "this kid is pulling a prank or harrassing the principal." I didn't sense that he was making a sincere request to the principal. The comment by Russ or Clint about him snitching seemed to support that. Will 1's action came across more as "just wait and see what happens". It may not be what you intended, but that was the image that was called to mind.
Will 1 needs some challenge early on. We need to meet Will 2 so you can set up the challenge for Act 2. And conventional wisdom says all that set up has to happen within the first 20 or so pages. So the challenge in book adapting is to figure out how to get the two Wills together and set up the driving conflict in twenty pages. Not an easy task. Do you need the set up with the Playboy magazine--really? Can it be made non-talking? The 'pick your friends nose' could be tightened.
We don't need to see them standing in line and sneaking in. The central point is that Tiny's dumped, gets drunk and ends up having his nose picked. It may mean shifting the order things happened in the book so that the Wills meet each other.
Don't misunderstand my comment. The writing style of the first 5 pages is good. But the direction it sets veers off. I expect the Russ and the others to become more integral antagonists. Were they on the same team? Then it's all about Tiny for the remaining 8 pages. It really needs to be about Will 1.
So you might just start with Will 1 getting up from the table and walking away as they glance at the Playboy. Nothing really integral was stated simply cut to a shot of him writing the letter and slipping it under the principal's door. While this is happening, you can have your V.O.
You might make it that Will gets a call from Jane that they need help getting Tiny home from the concert. Will goes but can't get in. A fight breaks out in the line and he manages to sneak in. We see Tiny lamenting and Will working with Jane and Gary to get him home. Now cut to the bedroom sequence.
Did we change the story? Yes. Does it have similar elements? Yes. Can we move things along quickly to the booger scene? Yes. Adaptation sometimes requires changing elements and order. No, it wasn't Gary and Tiny fighting, but it served the same purpose. Don't allow yourself to be trapped too literally to the book.
You have a good writing style. You'll need to evaluate, though, what is really relevant and interesting to put on the screen to get everything told in twenty pages so you can get into the meat of your story. Who are the protagonists, antagonists, and the initial challenge that launches the movie adventure? That's the first 20 pages. The rest of the fun is the next 70 or so pages.