What would you do if you were in my position?

Now, I see that this is young love. Ok, first thing first it's going to be a tease if the Drake is friends with your family. Now, to me it seems that Drake likes you but because there is so many people involved, he hides his feelings. You mention that he is shy and doesn't talk to you. Here what you need to do. You need to go to him by yourself and talk calmly and clearly. Just ask him if he like you as a friend or as a girlfriend. Then see were things goes from there. The down side to this is IF he say that he doesn't want to be your girlfriend then you can get mad. Good Luck, Hope that my information was go enough for you....