It sounds you want a relationship with him but he is hesitant. You are an analyzer and a planner and he is a spontaneous type. This can be overcome but you both have to deal with your issues in your own way. Your tendency to analyze does have to be monitored. It sounds like he wants a relationship with you but he is able to prepare for the worst. He has the friend role in his mind in case it doesn't work out. The problem with his philosophy is that if a relationship goes badly the friendship is usually damaged. I would give it a little time so that he doesn't feel that you are pressuring him. Slowly let him know that you need to know where you stand. I am not saying to just go with the flow indefinitely. Every person wants to know where the relationship is going. I would initiate a discussion when the relationship isn't as new. You should expect being in any relationship that you should be able to talk about it. If you work together on your communication you won't feel so anxious that you aren't supposed to ask the important questions.
Please press accept; this is the only way I am compensated