I thought most of it was cringe-worthy but funny, and I'm guessing that was their intent. Not liking him is unavoidable. It's almost like I wanted to feel sorry for him, but they show again and again he's an a*hole who never grew up. At least they also show how he got that way. He didn't seem to change much, but getting beat and humiliated let him acknowledge that he's been a childish d*ck. He was able to admit to his only friend about not wanting him to have a girlfriend. And while he was still obviously a control freak game master with the old folks, he could tell that his being a d*ck was turning them off to playing with him. Something he wouldn't see before that drove off however many friends.
I think Miles' character was there to start the fire kinda, even though it was Scott who brought him in. He should've went with the World of Warcraft kid, but the movie would've ended there with Scott continuing to act like a selfish d*ck and all around bad friend. Miles might have been a 'nerd', but they separated him from this group of 'loser nerds'. He was seemingly smarter, funnier, drank beer and had "problems" having too much sex with his girlfriend. He might as well have walked into a group of dorky 14-year-olds.
Scott's attempt to maintain his coolness factor with his fellow dorks in light of this Fonzie-like guy, only led to them seeing him for the d*ck he is. But at the same time we see that Miles is kind of a a*hole himself and really considers them losers when Scott points out he only put their video on his site to make fun of it. Ultimately if it wasn't for Scott's childish logic that Miles was his nemesis, and his failure to beat him, he wouldn't have been able to change, even that tiny bit. In the end I still don't want to be friends with him, but they show there's some hope for the guy. However astronomically small it may be.
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