what do i do now? need advice!!

I need to provide backstory in order for this story to make sense. I am a 20 y/o female, and this guy i'm talking to is my age. We met in elementary school, where we were good friends and stayed that way until he moved away. Mind you, we haven't seen each other face to face in nearly 10 years, and have just recently come into contact with each other via social media. I was the one to follow his account, but he was the first to intiate any conversation. So, we talked some during the summer, but then he went to military boot camp and the conversation fell off. What I'm wondering is multiple things: should i keep contacting him, since i am always the first one to text; could it be weird for him for me to keep messaging him? Secondly, the conversation he originally began with wasn't just "hey, how are you?", like he asked me about my life and is it weird that I find that attractive? The thing is we haven't seen each other in years, so I probably mean nothing to him. But i keep getting this feeling that i should keep trying to maintain contact? Any advice?