New Relationship: When Should You Have the Financial Conversation?

Not necessarily. The writer did not indicate any such behavior from this woman. He only said he pays for all their entertainment. If he had said she keeps asking for expensive clothes, jewelry, and luxury items, then you might have a valid point. Also, most men start out wanting to impress a woman, often by spending money to make up for perceived or actual character flaws, so he's not totally blameless for the direction his relationship has gone so far. If he has lived his life as a "chick magnet" then he shouldn't be surprised if he attracts the wrong element.