I'm glad others have the same take as I do about the paying for dinner scenario.

Here's my thoughts on it, correct me if this is out of fashion today:

If you ask him out, you offer to pay the whole check. He may insist on paying anyway.
If he asks you out, he pays the whole check. You can offer to pay half.

I never offered to pay half when I was asked out. Instead by the third date and beyond, I reciprocated by cooking meals, taking them places, buying gifts, etc...

If you start right away with splitting everything 50/50, the whole relationship becomes like that. When both of you make the same money, maybe that's a fair way to do it, but it makes the whole relationship dynamic more like friends to me.

When I was dating, I was not earning much money. When I dated men who earned a lot, they took me out and picked up the check. When I dated men who earned little, they took me out and we spent very little, if any money, and they picked up the check.