i don't know what to think, should i let him go

Still think you two could make it work or wanna give it a chance.. next time he contacts you, be assertive, and act as if you know you guys are meant to get together and tell him straight out.. I think its time when got together again and make it work this time..
See what his reaction is..
1. if he is silent then move on.. and let him go once and for all-- it could be that maybe he was just waiting this from you
2. if he goes along with it, then this is what he had been waiting for.. for you to make the choice and then he would too.
Good luck, you cant loose anything with trying, at least if it doesnt work you'll know that you really tried and wont wonder what could've been in the future..