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David Foster Wallace enacts in literature a discovery of what we are as selves in this world in isolation and community. Reconciling the two critical approaches to his corpus—Marshall Boswell's two-phase approach (2003) and Clare Hayes-Brady's recent single-phase approach (2016), I propose love as the singular target for Wallace's ethic and aesthetic of sincerity. Wallace's often-overlooked "Lyndon" (1998) offers a rare opportunity to freshly reassess the trajectory of Wallace's fictional oeuvre. Using touchstones of "self," "identity," and "naming," I draw on philosophers Amélie Rorty and Brett Bourbon. I illustrate how aspects Boswell claims as "later phase" are already incorporated in Wallace's early creative laboratory as Wallace pursues and displays this target of love through self- and relational identity. While accepting much of Hayes-Brady's analysis of integration of oeuvre, I resist her claims that Wallace's failure is intentional, showing instead that failure is not cause, but symptom of Wallace's search for a flourishing picture of love amongst depictions that are half-formed, malformed, jejeune, degenerate, or fake.