Lost in transitioning

This is sort of a 2 part question. To begin with, I have recently been getting some vibes and signals from my friend that he wants be more than my friend. But I am actually challanged when it comes to reading signals. He takes me out to dinner, and he wanted to come to my surgery with me and he asks me advice on really sensitive topics and compliments me...etc. As I wrote that it kinda seems obvious. But I dont no.
This brings us to the second part of the question. What should I do? He has been a friend of mine for a few years, so if we were to try dating how would we go about transitioning from freinds to more? And also, he is suuuper shy about this, he is like the perfect gentlemen but like he doesnt seem like he is the type who is gunna make the first move on a physical level. So what if I do and then I find out im terribly wrong about all of this? And also, how do I get over the akwardness of the fact that for the last few years I have thought of him as like my buddy and now I might think of him as more? and also, he is leaving for the whole summer in a week!
This is pretty much a clusterphuck.
Anyone have any advice??

He could be wanting to be closer friends with you. Does he have a girlfriend, if so, he probably doesn't like you like that. However, if he doesn't, then he almost definitely likes you. If you like him, you should try and start something. If you only have a week, get cracking, he would probably be very happy you made a move with him and if he only wants to be friends, just wait until he gets back and tell him that you still want to be friends