I think there is no way that Henry would be interested in someone like Ivy. If they are just going to hook up then fine, but as some sort of relationship, i just don’t find Ivy to be someone that Henry would be interested in spending time with.
I hate the whole connecting whether or not a female character is evil to her flirtation, but it is Ouat and Ouat is extremely backwards, so, of course, they are doing that.