[In a way, honesty can be a gambit, too. It doesn't escape Dazai's notice that John comments on this where he didn't flinch at double suicide nor gunshot wounds. If he were only saying that because it would be expected, he would have done so sooner. Dazai suspects he is indeed genuinely affected by the story, which tells him something about the other man in and of itself.]

He is.

[Dazai expects big things from him. The boy has a great deal of potential, if he could only find the self-confidence to grasp for it. Having him team up with Akutagawa is already moving things along, from what he can see. What had Mori said, back in the mafia? Only a diamond could polish a diamond. He looks forward to seeing the final cut that the two of them end up with.

But while they're being honest, Dazai skips the pointed insinuations and temperature testing and pushes them both into the deep end:]

What do you think of their warning, about midnight? If it was truly meant to protect us, why remain vague about the nature of the threat? It seems more designed to encourage risk-taking than deter it.