Yes many times and it's actually an awkward moment because while here on EF it appears that many men would like the woman to pay there are many that would not.
Simple rule to follow when in doubt: You ask you pay or at the very least offer up to split the bill.
When dating someone at least half the time I pay for dinner, lunch, movies etc - except in once case where my ex used to pat me on the head and say, "Sure honey, maybe next time." (He was much older than I and used to think my gesture was "cute" but ridiculous.)
I would like to think of a relationship as a partnership and you just split things, chores, monetary expense, oral sex, driving, food shopping and cleaning.
With the exception of only one dating scenario that did not allow me to pay on the first date. Actually - I snagged the bill from the waitress while he was in the boy's room and there was a huge protest (playful and fun actually) and when I wouldn't keep him money he was officially glued to my hip. (Not a bad thing)
Personally - I will never owe anyone anything ever - and that is not one of my better traits because it always gets in the way of a good relationship. As will the constant focus of "you better not make me pay too much before you put out for me."
My $2