Should i talk to him before i leave for the summer and he goes to basic training for six months?

there was this guy that i used to talk to every single day for about 2 or 3 months. and he reeaally liked me but i wasnt sure. He never blatently said he liked me but he would say things in an "arguement" like "wow i feel whipped" and other things too. And he would always text me good morning at like 6 am every day. But then he just stopped answering my texts. and a week went by and then he texted me and we talked for ten minutes and then he never answered my text.....its been almost three months. Im wondering if I should message him on facebook saying bye before i leave because he goes to basic training while im away and i wont have a way to contact him at all once he goes. And he will also be gone for six months. I just feel like I would regret not talking to him before i leave because i used to love talking to him and miss it a lot. Should I just let things play out and let him come to me even though its doubtful he will? or should i initiate something that maybe should have happened a long time ago back when the situation was fresh?