Pipaluk, with stuff like assassins, I generally prefer having a bit of a head's up.  Clearly, Octavian is primed to the idea that someone might try to kill him, which is why he is walking around with a bunch of thanes equipped for a fight, and there being someone to kill a nobleman is merely part of politics, really.  So are seductions and drugs, so I'm good with your character attempting all of those things.  ;D