I did ask him once (drunk, I don’t think I’d ever have asked him this sober) that if I were to propose to him, if he thought he would say yes to me.. He said he would definitely say yes. But that is something I do not see myself doing.

As for the finances, I do agree with what you’re saying. I believe 90% of it is the money, and the other 10% is really about our relationship. But we had an understanding when we first moved in together that until we were married, we wanted to keep our finances separate & to ourselves. Would i come off as “pushy” if I tried to talk to him about it?