Kit is disappointed in John because he is not assertive enough. He seems to have no mind of his own.
During the frequent heated discussions about politics at Matthew Wood's home, John seems to have few opinions of his own. Sometimes, he "seem(s) scarcely able to make up his mind at all" about what he believes. Matthew Wood would sometimes bait John "with fierce questions that (throw) the young student into confusion", and had labeled him "a young toady with no mind of his own". Part of the reason for John's extreme reticence is his unquestioning devotion to his teacher, Reverend Gershom Bulkeley - "nothing the revered Dr. Bulkeley could say or do could be wrong in his pupil's eyes, even the fervent defense of the King's policies which (go) against all John's upbringing".
Kit, who is in a quandary concerning her friendship with the Quaker woman, Hannah Tupper, needs someone to talk with about the matter, and had considered consulting John. Upon reflection, however, she concludes that "it would do no good to ask John about Hannah Tupper...whatever Dr. Bulkeley thought about Quakers, John would think so too" (Chapter 10).
John's reticence turns out to be a huge problem for him in another area as the story goes on. Because he hesitates in clarifying whom the true object of his affections is in the Wood household, he ends up receiving permission to court the wrong sister, bold and vibrant Judith instead of quiet and unassuming Mercy, the one he truly loves.