Oh, he can guess and this works to his advantage. While part of his interest in spending time with Katherine is rooted in genuine curiosity and honestly feeling bad for what happened to her (initially, for that which followed was of her own doing and frankly she deserved what came of her selfish actions), the other is purely for personal gain in the hopes of holding her attention to keep it off others and possibly get more information out of her. It's why he lifts a hand to her cheek for a moment, then drops it back to his side.

"I know."