him and rory have been into one another since they were teens. besides for a one month break up where she dated a cop while she was underaged, and got a stalker out of that, they have always been pretty solid with no drama. he went to jail due to hurting that same cop for trying to abduct them both from a public park. even though Michigan is a Stand your ground state, the attacker was still a former cop and on public property. so that's what he was in prison for. i think he would definitely prefer that she does speak her mind because he likes to know where he stands with people. tl;Dr he tries his best to treat Rory like a princess.