For an example of this, consider how he managed to get roped into any number of stupid, humiliating things over the years. Someone with two clues to rub together would clearly know that trying to play voyeur and antagonize Lawrence's step-sister would be a questionable idea at best and to avoid such messes in the future but since all he's got in between his ears is rancid lard, he comes to a stupid conclusion that means that yet again, his need to be popular no matter what the cost will set him up to fail again and again and again.
This stupidity of his also makes him think that he's far bigger a deal than he actually is. After all, when he isn't beefing about how Liz is trying to take over his life, he's complaining about how he's too cool and special and awesome to follow the rules like the sheep he has to waste time having to think about. It matters little that most people actually see him as the mascot of Gordon Mayes's army of social outcasts in the world in which we live, Tweedle-Dee the Wonder Dummy thinks that he's the best kid ever who everyone wants to shove into a corner because they're jealous.
That being said, he'd started to get a little bit better when he got out into the real world; had Lynn not gone crazy or had Karen Machette taken over, we could well have seen his short-sightedness, idiocy and callow arrogance moderate to the extent that he ceased being the Everykid foil to Elly and become the sort of bland everyman John failed to be because he's more an example of how unearned privilege corrodes character than a generic guy to identify with.