Even if the writer intended for this to represent how unsure Wyll is, this does not mean the protagonist - who is controlled by the player - has to be in agreement. There should be an option to tell Wyll to choose for himself.
At the core this is the same issue as with e.g. Halsin inviting himself into your camp. The writer does not consider what the protagonist's (player's) point of view of the situation might be. And that is not good writing.
