It's not a question of if Silver's attracted to him. She is, we know she's into men like him. The problem is, Asmon has admitted multiple times that, due to his own shitty childhood, he is incapable of feeling empathy for anyone or anything. His reaction to the hurt of others is usually frustration, annoyance, or apathy. The man called people who care about dogs getting killed "weak", interacted on-stream with his friend who was arrested for domestic abuse after he was in prison, and let his mother burn herself to death because he didn't want to take care of her. And, for as much as he likes to say he doesn't care, he throws a tantrum every time someone disagrees with him or criticizes him in any way. But hey, out-of-character Silver isn't exactly the best person either from what we know, so maybe they are meant for each other.