Both parties should come prepared to pay half. If one party insists on paying, the other party may allow it, but they should offer to pay on the follow-up date, if one should occur.Who does the asking is irrelevant. If my only motivation for going on the date is free food/drink, I should probably just say no.
or, if not a follow-up date, a 2nd round of drinks on the first date! yeah, if the date goes well, and you're going from bar to bar, it definitely doesn't make sense for one person to be paying for everything.