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The reception of Joe Brainard’s work, recently canonized in a comprehensive Library of America collected edition, has long been organized around a surprising rubric: the author’s niceness. Although it might seem that sidestepping the hagiographic attention to Brainard as a friend might be necessary to achieve a more accurate sense of his significance as an artist and author, this essay argues on the contrary that Brainard’s friendliness is in fact central to his aesthetics. The problem is not the attention to Brainard’s niceness but rather the assumption that this quality is a feature of his character rather than a particular sort of affective and poetic labor. Brainard’s work thematizes the relationship between generosity and creativity in ways that run parallel to Eve Sedgwick’s account of reparative reading, and his experiments raise similar questions about what it means to interpret the relation between sexuality and the aesthetic. “Friending Joe Brainard” considers these parallels through a close reading of Brainard’s most important literary work, the queer memoir I Remember, suggesting that Brainard mobilizes a queer form of tact to present a model of sexuality organized not around stigma and shame but rather around milder forms of embarrassment.