Life-writing takes many forms; William Hayley and his circle employed autobiographies, biographies, journals, letters, and memoirs to present themselves as they wished to be understood, whether by acquaintances or the reading public. Even objects such as gifts preserved memories of experiences; they could be “read” as evidence of the giver’s personality or intentions. Hayley played an important role in Anna Seward’s representations as friend, poet, and later, mistress of her father’s house, the Bishop’s Palace in Lichfield. In her critical biography of Seward, Teresa Barnard describes how Seward tried to “construct” her own life at a time when convention demanded she fulfill the roles of dutiful daughter and eventually, the wife of a husband chosen by her parents. Instead, Seward defied contemporary expectations in choices such as her life-companion and literary career. In journals, letters, poems, and even her will, Seward presented herself as she wished to be understood and remembered: as a principled, independent thinker, astute critic, and ardent British patriot. Instead, as Barnard details, Seward’s image and legacy were wrested from her by relatives and executors after her death (Barnard Life, 167–68). The editions of her poems and letters Seward intended as the foundation of lasting fame were instead prefaced as somewhat eccentric curiosities. But although her writings, which Seward considered her chief material remains, were tampered with, she also presented herself in a number of surviving portraits. While Barnard has discussed several of these, two of them form an opportunity to compare different versions of Seward. Painted six years apart by the same artist, intended for different settings and viewers, the portraits by George Romney show how Seward collaborated in adjusting her self-presentation depending on the context. In this chapter, Claudia Kairoff shows how these portraits marked important biographical episodes and commemorate her friendships with the artist and with Hayley, commissioner of the portrait that remains the poet’s best-known image. While composed in paint and not written in ink, the paintings convey important biographical information that would otherwise be missing from print and manuscript records of Seward’s life.