o.66-the maid, tried to play on the Prisoner's sympathies. She told him a sob story, that if he gave her some sort of information "they" would let her go. There was also tears, albeit them crocodile tears, but the Prisoner saw through this, and sent No.66 away with a flea in her ear, her services will not be required tomorrow!
No.9 also played on the Prisoner's sympathy at Cobb's funeral, and again there were tears, except they were real tears this time. Why was No.6 taken in by No.9 and not No.66? Well I suppose it was Cobb, the fact that they had both known him, that made the difference!
Be seeing you
I think the other difference was that No66 was sent by the Village and therefore it was self-evident to reject her, but when Number 6 saw Number 9 it was his own decision to talk to her.
Very best wishes
Yes, there is something in that. But I have the feeling that the Prisoner would have rejected anyone who asked him about information, whether they had been sent by No.2 or not. I think the real difference is, that No.9 didn't want anything from No.6 even though it was his own decision to speak to her, because they had something to share, Cobb's death.
Very kind regards