This might seem a bit random, and is related to my experience as a counsellor (as well as to more present meanderings):
I've been making a list of characteristics of real conversations. A provisional list (as should be obvious, as will certainly become obvious):
In a real conversation, wordless silence is respected. A participant who is uncomfortable, but finds it hard to say why they are uncomfortable, helps us to find the defects in our tools.
In a real conversation, there are no rules. The boundaries of the conversation are discovered, and sometimes these discoveries - when expressed within the conversation - can sound like rules. If we can break the rule and remain intelligible, then it is not a universal rule. At the boundaries, truth and intelligibility converge.
(Philosophy tries to give accounts of intelligibility and of truth as though they were, at root, different things. In specific contexts they may appear to be separate because a whole context can rest upon a false belief, but still remain internally intelligible. It is not possible to separate them for very general enquiries, however, where the only context is the possibility of articulated enquiry.)
A real conversation may project a metaphysics onto the world, but will never depend on one for its intelligibility.
In a real conversation, any metalinguistic enquiry is permissible, but the language of the present conversation (the one we are using to make these enquiries) is always at the top of the metalinguistic hierarchy. We can make judgements about the intelligibility of other conversations, but cannot question the intelligibility of the one we are engaged in. (Some very general statements about other conversations - e.g. 'Everyone talks at cross-purposes except for us' - are also likely to be unintelligible, but possibly not 'immediately'.)
In a real conversation, we exercise the Principle of Charity, we presume good faith, that we can make ourselves intelligible to one another, and that the truth can be borne.
Real conversations are punctuated by focusing episodes, as examined and explored by Eugene Gendlin, working with Carl Rogers.
Real conversations have more than one participant. This is not guaranteed by someone being 'physically present', nor ruled out by other participants not being immediately and physically present. My interlocutor is whoever reads this. It is not just someone in the room exchanging pleasantries.