My grandpa was always easy going early on in his marriage with my Nana. As they aged he got less easy going, but he's still a great guy, just more life stress and him expressing it.
It sounds to me like he does express his opinions and wants to some extent. He wants to make you happy and provide for you. He'd love to have a child with you.
I agree with an above poster that a combined amount for things like rent, house saving, and groceries is good cause then you both contribute equally, but with out the "his money, my money" thing. Yet you will still have separate accounts as well for other things.
I also like the idea of not stating your wants/opinions until you hear his.
But honestly, some people are really easy going. I don't care about what movie I go to see with a boyfriend, I don't have an opinion on where we go to eat (if asked I'll give a category like spicy or burgers, but not a place). There's other things I don't have an opinion on, and that's okay.
For the dinner example you mentioned, maybe ask his mom what his favorite food was as a child and then surprise him with it instead of having him ask for it.
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