having BEEN a shy guy (and still am in many ways i guess), there isn't much to understand. It goes something like this: oh i really like her, but i've known her for so long now she probably considers me as 'just a friend', and i dont have a 6 pack, i dont hang out with the cool kids at school, im such a looser that im browsing 4chan and laughing at web comics. <more rhetoric about lack of self worth> And shes so hot and 3 other guys are after her right now, plus i have to worry about school work and getting a job, and all this romance james bond stuff is just so unlike me and out of my character <more excuses for why the girl will not accept me>, meta-think myself into paralysis and oblivion

Well you only "cheapen" yourself because you're giving up power in the relationship by giving him the option to choose. But the thing is if he doesnt make the move, then he already considers himself unworthy, so you giving him power kinda shifts the balance back, in a backwards sort of way. You dont want to end up in a relationship where you make all the important decision, you want him to be doing 50% if not more. (That way you have the impression of being protected and secure, the whole damsel in distress paradigm) Perhaps the guy just needs a little nudge in the right direction.

important thing is how you communicate all this to him after the first step.