For me, I don't think he's hitting on Kory, I just hate guys who do the courtly goodnight thing. Quickest way for any guy to make me want to never see him or talk to him again is his ever using the term 'milady.'
As I said above, on the creepiness level compared to so many people in comics, this guy rates a zero. She's more just like somebody's boyfriend I'd find vaguely unpleasant to be around.