By the book
Kevin Ryan had always been the by the book good guy. At school he had always followed the rules even if he was a bit scatty, running around trying to find his textbooks in the morning after spending the early hours helping the less able students with their homework. He was always dressed smartly too, even when at the academy when they had downtime he had made an effort to be neat; dressing in smart chinos, casual shirt and polished shoes when the students went out or just socialised in the hallways or their rooms. Solid and dependable, that's how he always strived to be in life whether that be when being a prefect at school or the go to guy at the academy whenever inspections or tests were coming up. Ryan didn't mind his lifetime role, sure sometimes people took advantage of his good nature but that was to be expected and he never really took it to heart, if anything taking advantage of him meant that they weren't taking advantage of someone else.
However there was a downside to playing this role, he pretty much lacked any flexibility in bending the rules. It's not that he didn't ever wonder what would happen if he didn't polish his boots the night before parade or didn't play the designated driver whenever going out with people, he just liked the pattern of always knowing what was expected and where he fit into the world. Following rules had been a big part of him joining the police; he liked the idea of having a code of conduct to abide by and working with people who followed the same rules. The trouble was, as he found as soon as he started patrolling, was that some officers did not seem to work to the same code of conduct set out by the law and by the force themselves. There were deals made with lesser criminals in order to catch the big fish, lunch breaks were sometimes extended, blind eyes were turned when particularly nasty criminals 'fell over on the way to the cell'. Most of the time these deviations were done with the best intentions but Ryan still sometimes struggled not to think about it and feel guilty about not following the rule book. As he moved up the ranks and out of uniform Ryan began to get more comfortable with bending the rulebook in some circumstances if it was to protect another officer or victim, or to bust a really serious crime. Unfortunately, though the rule book was predictable, criminals and life in general was not and criminals certainly did not play by a lawful rule book.
Meeting Javier Esposito had developed him further in the being flexible and also started to get him relaxing more and seeing the lighter side of the serious work that was homicide. Esposito's background as a soldier meant he often saw the humour in quite serious situations and was able to make appropriate jokes in serious situations. Basically he taught Ryan how to not only do the job, but to not be a different person when you did it. If anything, if you let the job get to you and had to put on a mask to get through the day, the criminals still won even if you put them away. The good thing about Esposito was that he cared about his job and knew that the rules were there for a reason so he would never bend them unnecessarily and if he did there was always a just reason. Beckett was the same, though not as forthcoming with her humour until Castle had weaved the way onto the team. Montgomery had been flexible to a point as well though he had the political pressure to worry about and had always had to balance the rule book with that as well as looking after the team in general.
Yes, Kevin Ryan liked rules, order and structure. Being on Beckett's team had relaxed him and marrying jenny had opened his eyes to a world other than the police, but underneath he still craved the rulebook and knowing who to go to and how to act in certain situations. He didn't know what he would do if he was ever asked to break the rulebook explicitly by the people whom he had grown to admire and trust to give him counsel; namely Esposito and Beckett but Castle was as much a part of his family as the other two. Hopefully that day would never come but Ryan had a feeling that something was coming and that his question would be answered sooner rather than later. He could only hope he would make the right choice.