Charlotte’s Web (1952) by E. B. White is a classic children’s book praised for the memorable friendship between its two protagonists. This article explores the problematic bond that results from Wilbur’s greater demand on Charlotte and Charlotte’s act of devotion. It also examines the moral value of humility, from the word “humble” which Charlotte weaves to praise Wilbur, which can be questionable as it is intertwined with innocence or ignorance, and better suits Charlotte who is reticent of her accomplishment. That she must pass on without recognition casts doubt on the author’s presentation of friendship and the said moral value. Looking beyond White’s fictional work, it is not surprising to discover his lack of respect for traditional morality. Even so, the article finds that White does offer certain moral guidance to his young readers, but it is far from straightforward due to his frequent employment of evasion, humor, and irony.