Henry is so twisted, he despises and holds in contempt the women he so heartlessly pursued. There does seem to be a tinge of bitterness here- I wonder where it comes from.

I am not sure he would have been happy if Maria had given up her engagement- for after all, he would be indirectly implicated in it. I believe he judged Maria's character correctly and realized that she would chose Sotherton even with a broken heart.