This chapter explores the specific challenges that cognitive science and social psychology pose to those literary concepts and modes that are grounded in traditional moral understandings of selfhood and action, including integrity of character and notions such as tragic realization and moral repair. Focusing on the concept of moral time, the chapter explores two literary texts in which profound middle-of-life dramas take place: Henry James’s “The Beast in the Jungle” and Shakespeare’s The Winter’s Tale. A form of slow psychic time entirely lost to view in recent cognitive science is shown to take place in James’s tale, while The Winter’s Tale insists on the forms of moral and emotional experience that are beyond reflection and explanation. The readings presented are set in relation to key critical debates on the works, to challenge a persistent evasion of moral frameworks in contemporary anti-normative approaches.