Pretty sure it's basically them using "Are you used to [this]" and "Have you made any progress [with that]". In Japanese, if the context is known, you could use the same sentence to talk about a thing, a person or an activity etc... which leads to many misunderstandings.
"Have you tried.... it?"
"Yes, many times!"
One person is asking about kissing, the other about baking cookies. In this chapter, one person is talking about mysteries, the other about Toiri, and they sort of rammed into each other in a head-on collision.
Except they are not, since both of them neither provided a context, nor bothered to ask one. Try reading the dialogue without the inner thoughts: the first reaction of any normal person is "the fuck are they talking about?"
Imagine the scene: you are minding your business, when out of the blue your friend ask you: "did you do it?"
The normal reaction is: "did what?"