It means that he still feels something for you. Saying you go separate ways meant that you should not be together again and now that he keeps messaging you is like he likes you. It's good you approach him and ask him what exactly he wants from you.
you obviously have a hold on him in some way...... because he keeps contact. or he could just wanna c how you react/stand with the situation and go from there. you need to decide if its worth it. he doesn't sound very mature. just saying.... guys who play with ur mind are bad business girl. livin is learning though so best of luck to ya!
He obviously doesn't think of you in a romantic sense any longer, yet doesn't want to end a potentially decent relationship. That would be up to you. If you still have feelings for him, in a more than a "friends" aspect, be honest and tell him that. Sometimes it's better to part ways and move on. You sound like you might still be feeling more for him, than he does for you. You are the only one who can answer hat. There is nothing wrong, however, in still being a good friend and nothing more.