The Portrait of Lambert Lombard of circa 1560 is unique among early modern likenesses in its intimate portrayal of an artist as friend. This essay moves beyond the questions of attribution that have hitherto dominated discussions of the painting and focuses instead on the dialogic encounter the image establishes between sitter and beholder. That encounter, I contend, reflects a novel period concept of friendship as a social ideal and as a model for artistic practice. Working within humanist frameworks, Lombard’s pupils actively constructed an image of their teacher as scholar and affectionate pedagogue. While other images of Lombard emphasized the artist’s erudition at the expense of his personal warmth, this disarmingly nonchalant portrait negotiates a balance between the aloof scholar and engaged friend. Like Dominicus Lampsonius’s biography of the artist, published in 1565, the Portrait of Lambert Lombard envisions the artist as a friend who is both erudite and loving.