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Will is the first of the two Will Graysons that we meet in this story—this is capital letters Will—and while at first he seems like a pretty typical kid, that doesn't mean he doesn't have stuff to deal with. Do tell, Will Grayson, do tell.
Will's been raised in Evanston, a Chicago suburb, by parents are busy doctors but also pretty darn loving. Even though Will has lived in Evanston his entire life, he only has one actual friend—the one and only Tiny Cooper:
When I was little, my dad used to tell me, "Will, you can pick your friends, and you can pick your nose, but you can't pick your friend's nose." This seemed like a reasonably astute observation to me when I was eight, but it turns out to be incorrect on a few levels. To begin with, you cannot possibly pick your friends, or else I never would have ended up with Tiny Cooper. (1.1)
You'd think having the same best friend since the fifth grade would be an awesome thing, but not for Will. Tiny is one of his problems because he constantly overshadows Will with his larger-than-life personality.
Tiny's only one of Will's problems, though. He's also terrified of heartbreak. In fact, Will's so freaked out by the thought of putting himself out there and letting people in on what he's feeling that he lives by some very important rules. Check them out:
Tiny thinks that I am incapable of what humans call emotion because I have not cried since my seventh birthday, when I saw the movie All Dogs Go to Heaven. I suppose I should have known from the title that it wouldn't end merrily, but in my defense, I was seven. Anyway, I haven't cried since then. I don't really understand the point of crying. Also, I feel that crying is almost—like, aside from deaths of relatives or whatever—totally avoidable if you follow two very simple rules: 1. Don't care too much. 2. Shut up. Everything unfortunate that has ever happened to me has stemmed from failure to follow one of the rules. (1.10)
Ugh. This does not look good. Will Grayson is intensely invested in smothering his feelings.
Okay, so aside from keeping Will from crying over something as traumatic as All Dogs Go to Heaven, what do these rules exactly mean?
Well, they mean that Will can't date anyone—especially not Jane, whom he clearly likes—because it could all end badly. He can't get too invested in Tiny's play either, because he just knows it's going to turn into a mess. And he definitely can't let his best friend know how much he loves and appreciates him—that would just be a disaster. For Will, not caring is the way to go. As he says,"caring doesn't sometimes lead to misery. It always does" (1.77). You sure about that, buddy?
See, even though Will tries to keep all his feelings inside to protect himself, he gradually finds out that this is not the smartest move. After all, if you shut out everyone to avoid ever feeling bad, then you're also keeping yourself from ever feeling good.
Will ends up making himself miserable when he passes on dating Jane. He can't stand the thought of potential relationship drama, so he just gives up on the idea of love all together. He also ends up giving Tiny the cold shoulder so that he doesn't get sucked into helping with the production of Tiny Dancer. Will also tries to get Tiny to dial back things with the play at every step. Especially the stuff that involves him:
"I'm gonna need you to be in the play."
I stifle a laugh, because this s*** won't be funny anymore if it's staged in our goddamned auditorium. "Absolutely not. No. NO. Also, I insist that you write me out of it."
Tiny sighs. "You just don't get it, do you? Gil Wrayson isn't you; he's a fictional character. I can't just change my art because you're uncomfortable with it."
I try a different tack. "You're gonna humiliate yourself up there, Tiny."
"It's going to happen, Grayson. I've got the support on the student council for the money. So shut up and deal with it." (5.52-56)
But none of this actually keeps Will safe. He ends up realizing what he's missed with Jane once she gets back together with her ex-boyfriend. Likewise, when Tiny starts shutting him out, Will begins to understand how much he needs his best friend in his life. In short, in committing to not caring about both Jane and Tiny, Will comes to see that actually he cares about them a whole lot. Oops—looks like Will Grayson is about to learn a big lesson.
By the end of the book, Will has finally given up on his crazy rules. He knows that he can't just hold everyone at arm's length and expect to be happy; he has to be open to the possibility of heartbreak in order to find the good stuff. It's like he tells the other will grayson:
WGrayson7: but i think the point is that it's not just try-error.
WGrayson7: most of the time it's try-error-try
WGrayson7: and that's how you find it.
WGrayson7: you know. it.
willupleasebequiet: yeah, it.
WGrayson7: well... i haven't become that optimistic.
WGrayson7: it's more like try-error-try-error-try-error-try-error-try-error-try... at least fifteen more rounds... then try-error-try-it (18.28)
This means Will's ready to be with Jane and give love a chance. He's also willing to apologize to Tiny for acting like a jerk and finally tell the truth: He actually loves the big guy a ton. And when Will finally sees Tiny's play on opening night, he realizes why he and Tiny are friends—they do care about each other and have each other's backs; they always have.
This kind of stuff wouldn't be possible for the closed-up Will Grayson at the beginning of this novel. Like he says in the end, "I guess I'm not the Will Grayson I used to be" (20.37). So true, Will. So true.