I think the new Nameless visit does not happen when you accept the witch'es help. Or maybe I just don't know how to trigger it. Hovewer, if I reject her help and go to sleep, Nameless appeares and asks me questions. First time he gave a few options, when he asked what I really care about, and I saved the game before it. But each time I use that save and want to check the options again, there is some "boom" happens (after drip drip drip) and instead of different answer options, I see "Did you really think your tricks would work on me every time..." even though I did no tricks. I think it's some sort of bug.