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Talk to him!! Just go for it. If it doesn't work out, then you don't loose anything. You'll just be back to where you are right now, and it's not that bad. But if you both are interested in each other and it works, it'll be great. You don't have anything to loose. Start talking to him more, make...

It depends on how far away he's going, how often he'll be coming home, what his interests are (to see how much time he'll have) Most of all, you need to talk to him about this. You need to know how he feels about long distance relationships, how he would handle one, etc. If he's going to college...