I dunno. It seems to be rather culturally dependent.
Also, I've never been on a date, like, ever, so keep that in mind too.
I'm part dutch. And the dutch have an odd reputation for being greedy / stingy.
One thing of note is that I believe splitting the bill there would be considered the norm, rather than the exception.
That aside, personally, I'm uncomfortable with someone paying for stuff for me, generally.
But as to what kind of message that sends, I don't know.
And as I said, I have no experience at all with doing such things in a romantic/dating kind of context, so... I don-t reallh know.
But subtle cultural differences do matter.
(Also, given what most cultural expectations revolve around, I sometimes wonder about same-sex couples. Possibly because I'm bi and could run into that situation in theory... But seriously, what do you do with customs that assume specific roles defined by heterosexual identity?)