Character Analysis
These two guys are will's friends from school. Though it's not as if will has a super close relationship with them:
i sit with derek and simon at lunch. the way it is with us, it's like we're sitting in a waiting room. every now and then we'll say something, but mostly we stick to our own chair-sized spaces. occasionally we'll read magazines. if someone comes over, we'll look up. but that doesn't happen often. we ignore most of the people who walk by, even the ones we're supposed to lust after. it's not like derek and simon are into girls. basically, they like computers. (2.28)
Basically, these guys are sort of safe friends for will to hang around. They aren't into girls so will doesn't have to worry about one of them asking him who he has a crush on. They're also mathletes, which means we can assume they're pretty close to the bottom rung of the social ladder in high school. (Sorry, mathletes. For what it's worth, mathletes are really high up in Shmoop's heart.) So by hanging with these guys, will doesn't put himself at risk at all.
Will's big moment with Derek and Simon is when he finally comes out to them. This is when he actually risks opening himself up to these guys he sits with at lunch every freaking day. While Derek is pretty nonchalant about it, Simon is a little less accommodating:
simon: so how was your big date in chicago?
me: do you really want to know?
simon: yeah—if it was big enough for you to bow out of our competition, i want to know how it went.
me: well, at first he didn't exist, but then he existed and it went pretty well. before, when i told you about it, i was really careful not to use any pronouns, but i don't give a f*** anymore.
simon: wait a sec—you're gay?
me: yup. i suppose that's the correct conclusion for you to draw.
simon: that's disgusting! (12.46)
All in all this is probably the most homophobic thing that happens to will in the entire story, and will is able to talk Simon down in about two seconds by suggesting that he is also attracted to guys… even if they happen to be warlocks in a video game.