Viewing Othello as the drama of epistemology and human certainty, this work analyzes Desdemona, Othello, and Iago as distinct but similar portraits wherein self-esteem and the existential self-image wax or wane with extremes of belief and disbelief in the possibility of the marriage of minds. The author’s thematic and generic comparisons of Othello to The Tempest, A Winter’s Tale, and especially to Sonnet 116 and Cymbeline illustrate that knowledgeable certainty lies in both the skepticism and the humility of the Christian thinker who does not deny human potential for the sake of the image.