ideally both ppl in the dating scheme want to pay for things b/c they genuinely like each other and want to do for each other and not b/c they feel obligated or are afraid of being seen as __ or __. it should be natural. it shouldn't be complicated. if it's complicated the ppl involved should definitely be talking about the complications.

i dated a guy who made lots more money. i let him know i wanted to pay sometimes (b/c i liked him and wanted to do it) but that i couldn't pay as much as he could and i feared he would think i was taking advantage. i put it right on the table and we addressed the issue. we worked it out.