Interactive Freeform Quiz

Hello all, I was wondering if you could help me please? I have an idea in mind of 2 characters talking, but I want to make it so the user selects which questions the first character should ask, based on the 2nd characters answer.

I'm familiar with how to create a scenario of 2 characters talking and using the timeline and animation features to have their respective caption boxes appear and disappear as new caption boxes come up (like watching a comic book in a single frame essentially) and I've briefly toyed with how to create a basic freeform quiz.

Is there a way to make it a timed freeform quiz? Ie, I provide the first question like so:
character 1 "question 1"

character 2 "answer 1"

then, to continue, the learner would then hover the mouse over the caption box for character 1, and select from say 2 options (shown while in hover), then once selected, character 1's caption box would change to 'question 2' and the 2nd characters caption box would provide the response if it is correct, or say 'sorry, try again'

or something to that effect?

Or is this a little too complex for storyline?