Will he ever Propose if he hasn't already?

If money is tight, could you forgo any ring at all? If you want the commitment, and he says he would be willing to get married, you don't need a ring to say that you're "engaged," as long as you both agree that you are going to get married. As for getting married, if you can both be satisfied by going to the courthouse with your kids and close family, maybe you can convince him that there's no reason to wait. Years from now you can have a vow renewal when you don't have two young children to care for.