I think it's a bit old fashioned and impolite to assume that the guy will always pay for you. Not everybody is always in the financial situation to be able to pay, but that doesn't make them a person not worth dating. If he's making it a point to not pay so that he can mooch, that's a different story though.
I always operate under the general process that the person who invites the other out to a place requiring money (dinner, a movie, etc) will be the one paying unless you've agreed earlier to go dutch on things. I think it's just fair that way. Relationships are a two way street.
If money is an issue, why don't you try doing things together that don't require it? Just going out and taking a walk together, things like that.