This chapter thinks about the risks of becoming enchanted by Whitman’s writing. Under crisis neoliberalism, “risk” has become sutured to a phobia of being exposed as naïve; it is often risky to not have some explanatory framework or incisive critique at the ready. Of increasing resonance at this political juncture is what this chapter thinks of in terms of Whitman’s “grammar of risk.” To read Whitman’s poetry now is to feel the jolt of a form that momentarily suspends a language of looking through or beyond what is in front of us. This is not to advocate a “surface reading” that necessarily cancels political depth, but rather to think in terms of a surface consciousness that always imbues a moment of contact with the dignity it might deserve. This is an attitude towards others that continually risks disappointment, but it might also be the only nonviolent way forward we have.