Bobby had been splitting his time between the Roadhouse and the Winchester homestead. He was honored that John offered him a room in their household-- it really did feel like one big family over there.
He happened to be at the Roadhouse when Mack came by. Bobby wanted to make sure that it was as secure as possible, what with Lilith still out there. Focusing back on Mack, he wasn't sure what to do-- what he could do to help the boy. He'd lost a friend, a teammate and Bobby knew how hard that had to be. He hadn't gotten the chance to really get to know Kira before Lilith had taken her from them. For that, she was going to pay. Bobby would make sure of it.