He wasn't very showing with his emotions but he was observant to others. When she started crying which he could easily tell she was, it was awkward to say the least. He wasn't good with people crying let alone women crying. He didn't know what else to do other than to bring his arm around her shoulder lightly. Also standing there like that awkwardly.

He shifted his eyes to her " Are you okay?" people were not his strong suit really. " Yes, crying is silly unless you have a reason for it. So...I am asking if something is wrong?" Aww look the emotionally constipated mafia prince was trying.