I could totally see Kit be the type of person that just annoys the shit out of Connor almost unintentionally, because Connor's more about action and Kit's almost the complete definition of passive. Connor might intimidate the hell out of the poor kid, but maybeeeee, just maybeeeee Kit's good nature might wear Connor down.
An alternative, or even an addendum, could be that perhaps Connor and Kit's brother were close. The brother was a much less meek person. All about kicking ass and chewing bubblegum, but eternally lacking bubblegum, except when it came to his kid brother. Seriously, Kit's got eyes like Puss in Puss'N'Boots sometimes, at least when it came to his big bro.