I think you need to figure out what you want, a friendship or a romantic relationship and a friendship. If the friendship part is most important to you, I would wait and let him make the first move, but give him subtle indications that you are interested. If a romantic relationship is your real concern, I would be more forward because you would have nothing to lose. If he is not interested, he will let you know and you can move on and not waste any time. You say you are already dating. I don't know how long this is for, but if he is not giving you indications of something more serious, either he is afraid and has relationship problems (which should be taken seriously because this could signal problems in the future), he has been hurt before and wants to take it slowly (which is fine, but he should let you know), or he is not interested in pursuing this much beyond what it is. Since you seem to want more, I think it is important to find out where you stand now. Plus, my experience has led me to believe that you can generally tell how someone really feels about you. Does he call you all the time and want to see often? Is he open? Does he play games? Do you find yourself waiting by the phone and he does not call?