Well, at least he was smart enough to finally realize the two big reasons she was assigned to him. Not actually sure how smart bringing her to Kurokochi's bar is; if she was going to wiretap a place beforehand, she would've done it there too; if the bugs were removed, she'd know and get suspicious; and if she wasn't going to, then going there had no point. In any case, letting your enemy know about one of your safehouses is never a good idea. At least he got saved by his boycrusher.
I have no idea where the arc with the PS is going. Cult asassinations? And this is something deeper than the Sakura Council? Is this supposed to be like a Shinzo Abe/Unitarian Church type deal?