What does it mean to be a friend in Shakespeare's England? In their writings on the subject, Renaissance users of rhetoric would recognize, deploy and appreciate tropes and textual ambiguities in a manner alien to twenty-first century readers. The large body of classical writings on friendship which cropped up on early modern school curricula, especially Cicero's productively paradoxical De Amicitia, provided imagery and scenarios which could be recast by fertile imaginations. This inventive use of tropes and contradictions when writing about friendship has important parallels for queer scholars. The problems and benefits of asserting a 'queer history' are considered here, as is such a history's ambiguous relationship to historicist reading practices. Texts examined include three 1580s conduct books on friendship; John Florio's translation of Montaigne's essay on friendship; later English essays on friendship by Francis Bacon and his contemporaries; the correspondence between Edmund Spenser and Gabriel Harvey; and Shakespeare's Hamlet, King Henry IV and Sonnets.