It seems that here is a lot of confusion and uncertainty that you are trying to handle on your own but he has 50% of the answers. When this happens you have to take a step back. Pursue this gently You are walking a fine line between starting a relationship and having this problem at work (I am not sure what you do).
This has to be a risky situation. I am not sure how far you can push this. Work/personal hardly ever works out. Communication is the only way to resolve things