I agree, I do think Henry must enjoy the "hunt" and also really likes to keep his options open. I can just imagine a bit of his thought process... Here is Maria - a beautiful, rich young girl who does seem to be throwing herself away for money and security... perhaps he can string her along a bit(and have her enjoy it too!) to make her change her mind, and if nothing else comes up better, she would be available to him. I don't think he's thinking too far ahead, either. Henry and Willoughby from S&S are similar in this respect. And there are similarities here, too, to Frank Churchill, who didn't mind the flirt/hunt/dance/mating game, either.