This dissertation explores how Robert Frost, Wallace Stevens, and John Ashbery have responded to the problem of philosophical skepticism that they inherit from Emerson: that while things do in fact exist, direct knowledge of them is beyond our ken. Traditionally read within the framework of an evolving Romanticism that finds them attempting to resolve this problem through some form of synthesis or transcendence, I argue instead that these poets accept the intractability of the problem so as to develop forms of thinking from within its conditions. Chapter One explains why poetry is particularly suited to this sort of thinking and what it can achieve that philosophy (or at least a certain understanding of it) cannot. Chapter Two focuses on the act of listening in Stevens’s poetry as a way to show how Stevens is not, as is typically thought, interested in “the thing itself,” but in "the less legible meaning of sounds," the slight, keen indecision that resonates in between sense and understanding. Chapter Three focuses on those moments in Frost’s poetry when, instead of attempting to comprehend, seize, grasp, and represent reality through the use of metaphor, he chooses to regard its inappropriability or otherness. And Chapter Four focuses on how Ashbery’s constant shifts of focus are not just the wanderings of his mind, but a technique for disrupting our absorption in a single plane of attention so as to achieve new economies of engagement. Overall, though, the goal of this project is to move the discussion about this line of poets out of the epistemological register within which they are usually read and into an ethical one.