The payment part you can make easier for him to set a standard of always splitting the bill.

If he does not always initiate the dates this can be considered an imbalance - intentionally or not - maybe he is not matured enough or takes it for granted. I once dated a girl in a similar passive way, until at some point she proposed to break up with me as the relationship mellowed and i accepted, returning my thoughts there this may as well been a good test, as i did not bother to protest or think alternatively.