For me when I take someone out on a date I am going to be the one paying. If person wants to take me out on a date I expect them to pay. In my book it is the person who asks the other out that pays for a the date. Now if it is just a couple friends meeting someplace then that can be open for more discussion or each person paying their own way. I know there are some that do not like someone paying for them and I can work with that.
If it's a romantic date, I was raised to believe the man is suppose to pay. But if it's friends you usually split the bill unless an agreement is talked about before hand.
Culturally, at least for romantic dates, it has been taught men should always be the one to pay. Though in more recent years this idea has been challenged by many women and others Some some even arguing for a 50/50 slip of the bill or to switch off. Which is why I think this might be something to discuss with someone you want to date.
Perhaps, but even that could get you in trouble. As while you and your girlfriend/boyfriend or spouse are okay with just having whoever makes more pay the bill for the date… If it is the guy letting the girl pay, he's likely to be criticized by others.
I haven't dating in a long time, but my view on it now is that it's something to be discussed beforehand. It's not my place to say 'you should do it' to a couple on a date. For me, it depends on who has the money, whose idea it was to go on the date, and other circumstances.