Exactly my point!
Since talking is tied to reputation level only ... you can (and with Gale often do) get to sitation where you are:
Approval > congratulation you just unlocked new cinematic conversation, but we will never tell you.
Approval > congratulation you just owerwrited your previously unlocked conversation with new cinematic conversation, but we will never tell you.
Disapproval > congratulation you just lost your unlocked cinematic conversation ... of course you dont get back that previous one.
In my honest opinion best way would be:
You click long rest ...
Event that should be happening is happening (sick night, raphael visit, surprisingly handsome elf ambush, ...)
You come talk to companion ... reactions for event happens ...
Then IF there is no reaction on event (or is event that dont require futher comentary ... i mean it would be odd if our companions stopped "feling sick"

... but not so odd, when attack of surprisingly handsome elf is done)
> Game checks what was your last cinematic conversation with curent companion ...
> Game checks if your aproval is high enough for the very next in line (they would need to be coded in specific order)
> Next conversation is happening, or regular generic "how can i help" starts.
That way we would not skip cruicial parts of your relationship development ... and we would be able to talk with multiple companions within single night.