I always think that lying to make someone feel better, is disrespectful.
So i am always blunt, or try to say the truth in a softer way. But i wouldn't hide it, ever.
And that's the same with enabling. But if i know the other person understands the consequences of his actions and that i wont be used ungratefully, then i will engage in his enabling behavior, because that is his choice.
Even if i dislike it, if i respect the person, i should respect their choice, but make boundaries and make sure they understand their decision.
Unless i think they are incapable of making a good decision. But that would be rare, who am i to know what they need in life?
Being asked a question while expecting a specific answer terribly annoys me. I would answer what the other party least wants to hear, just to get back at their manipulation.
Being guilt tripped makes me most angry, its very likely to produce the opposite effect of a guilt trip: