Sounds like this man was raised with good morals and high character traits. He probably is old-fashioned and of the belief that a man should take care of a woman, and that's why he insists on paying for all of the dates. It's probably something you may want to discuss with him in another setting other than when you are out to eat, as that can make for an uncomfortable situation.
Let us know how things work out in the end.
Matt
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