This worked for me and my bf, first get to know him, this will make it less awkward on your first date sense you know what to talk about. Then start to flirt and be very nice. Then when you think you are both ready ask him if he likes anyone. If he says yes but won't tell you, start to talk about how you hate it when guys make girls make the first move. Then if your ready and tired of waiting ask him out. Thank you for reading this all the way through! :)
I was in the same situation just a little while ago. We both liked each other but we are both super shy. His best friend would set us up on double dates and he would actually take our hands and put them together so we would hold each others hands. I really wish I could've asked him out or done something before that because I was waiting for almost a whole year. So totally go for it you have nothing to lose!!