When trying to think of questions to hypothetically ask Viola, it helps to consider things like her characterization and especially why she is important to the play and how Shakespeare uses her. What is Shakespeare trying to show through her character?
One thing we know about Viola that's central to the story line is she disguises herself as a boy. We also know from the play that Shakespeare uses her disguise to show the underlying consequences of deception. We especially see the consequences portrayed when Viola realizes that Olivia has fallen in love with her. Viola contemplates how, just like Olivia is breaking Orsino's heart, Viola will inevitably also have to break Olivia's. Hence, she sees just how much havoc the act of deception can cause, as we see in her line, "Disguise, I see, thou art a wickedness" (II.iii.26). Hence, knowing that Shakespeare decided to disguise Viola for a reason, and knowing that Viola also learned something from her disguise, one legitimate question to pose would certainly be:
- What did you learn from disguising yourself as a boy?
We can also contemplate Viola's personal reasons for deciding to disguise herself and ask something like:
- Why did you decide to disguise yourself as a boy?
We can also analyze her characterization by considering things she learned from certain moments in the play. For example, the moment Sir Andrew challenges her to a duel was a particularly trying time for her. Hence, we can wonder if at that moment she wished she had not followed through with her plan to hide her true identity by pretending to be a boy servant and asking something like:
- Was there a moment when you wished you had never decided to disguise yourself as a boy servant?
We can also contemplate the things she learned in the moment that Sir Andrew challenged her, such as bravery and perseverance, and ask something like:
- What did you learn about yourself the moment that Sir Andrew challenged you to a duel?
Hence we see that by contemplating what Shakespeare is showing through Viola's characterization and even Shakespeare's overall points and messages, we can easily think of questions that relate to Viola.