That’s great that you are aware of your co-dependent tendencies and working on yourself! It does appear that you have an anxious attachment to this guy, so “playing it cool” is not the route to take with him. You actually should be opening up your feelings to him no matter how uncomfortable it may be. Otherwise, you prolong this feeling of un-fulfillment with him. You might as well find out where you stand and be truly free to move forward with him or without him. That is true independence.