@Lucia
You should successfully poison the carafe.
@RockStar
I think to get Die Smiling, you have to have a high magic stat and not break his control over the Monarch’s mind (and I think you should break it over his lackeys) and then choose that option where you have to kill him or your family will be unsafe and it should ask you if you’re willing to go through it because it’s such a risk, and then you accept. Something like that, I can’t remember exactly.
EDIT:
I’m missing 2: *Freedom and Revenge and I’m also missing If You Stab at the King, You Must Not Miss . I tried with Subtletly 22 and failed to get it (aka I killed him but got caught) so I guess it has to do with a bad relationship with the Monarch and do I have to let him be unfaithful, too?