We've gone out a few times, and those times I've asked him out. I made a joke to him that I would be waiting for him to ask me the next time and he agreed, but he has yet to ask me and it has been some time. He does work two jobs and goes to school. whenever we see each other our conversations are never awkward. We always ask about eachother and our lives and can always keep the conversation going. Our first outing was suppose to be coffee (I had asked him to meet up for coffee) but he ended up asking me to lunch instead. And the second time I asked him to lunch again. He seems interested by responding to meeting either that same day or the next day. How long should I wait for him to ask me out? Or will he even ask me? HELP!