Well, I think the one who would like to pay should pay.
At my first date - with my recent boyfriend - I saw at his face that he would like to pay, for reasons that felt good for him.
Nowadays sometimes it's my turn to pay, other times it's his turn again. Actually it is just something we could discuss, and just talk about it. Very easy.
- Sorry if there are mistakes above here, I'm practicing my English this way -