Pruuuuue. Oh, man. So, at first, of course, he was hesitant to get too close because old habits die hard, and. Witch. But, he's the more understanding brother, or at least, the less prejudiced one. Prue turned into a conversation partner, a friend, a confidant. And then, a few events later... they're in a not-relationship. He's not sure what to think, so unsure, and the least of his worries is what his family would do if he was dating a witch. After Ruby, he's wary. After Madison, Jess... he's terrified. Dating anyone is an automatic guilt trip, because he's so afraid they'll get hurt because of him.

But, she's something else. Something warm, and real, and not like he's really used to. He can almost forget that he's worried for her, that something could happen to her, because she takes him away from the details of back home. But, she's a seriously important person to him, and though he might not admit it to her, or to himself, he could date her. He'd like to, because she makes him that happy. But... getting him to admit it, to own up to it? That's another thing.