He seems like the type to go for busty curvy women.
I know this might sound like a strange thing to say, but do you
think many men date her for the sake of being able to say 'I
dated Paris Hilton' ?
If you don't know what I mean by that, say you have someone
who dates only the 'best', if they went after you, you might date
them not just because you like them but because of the
attention that comes with it. Does that make sense?
Or maybe he genuinely likes her.