James is a pensive boy confident of his mental capabilities but less confident of his social standing among his peers. Of all the Tillerman children, James suffered the most greatly at being an outcast as a result of Momma's unconventional lifestyle, and he more than any of them sees Crisfield as a chance to start over without the dark cloud cast by Momma's well-known eccentricities hovering over them. Dicey has always worried about James's ability to divorce himself from morality or emotion with his intellect, and his ability to use his intellect to find means to his own ends. James faces two major challenges in the course of the novel, both of which illustrate his shortcomings and his strengths. First, James wants to make friends, and to do this, he learns to act as though he is not as smart as he is in school. The boy he befriends, however, is also a cerebral and scholarly boy, and James does not have to change his interests and activities in order to be the boy's friend. Second, James assumes the responsibility of helping Maybeth learn to read. At first, he shirks this responsibility in favor of spending more time pursuing friends, but in the end, he applies his mental keenness to Maybeth's problem with skill and perseverance. James works to balance his desire to be well liked with his desire to be a loving and responsible member of his family.