
I think it's just cuz he's not sincerely in love with her yet nor is she with him. He certainly likes her and is possessive/obsessive of her since she fits his criteria perfectly (dummy mommy, sexy, proud and not afraid to speak her mind, etc), but its not love yet, they haven't had time to make that connection. So he sees her as not necessarily an object, but as an asset/posession I guess? I think that's why his wording makes you feel uneasy because he's always assessing her and if she is what he wants, even now, something Courtney is acutely aware of. I'm sure as they progress as a couple it won't feel so uneasy as he falls in love
I don't know but Richad give me mixed feeling. His word a little bit doesn't feels right to me. I hope nothing bad happen :)