The word “alone” recurs more frequently in Shakespeare’s Sonnets than in any of his plays, but even as the Sonnets produce expressions of loneliness easily understood by twenty-first-century readers, they also bear witness to its cultural and historical contingency. This chapter isolates three moments in the Sonnets’ reception history when their loneliness is a matter of debate, explored particularly through Sonnet 29 (“When, in disgrace with fortune and men’s eyes…”). We begin with late sixteenth-century Petrarchan love lyrics, in which loneliness is an affective pose, but find that Shakespeare’s Sonnets are shot through with sexual and status anxieties that did not trouble Petrarch. By the Victorian period, the loneliness of the Sonnets belongs firmly to Shakespeare himself, which produces a potential conflict with his reputation as a national poet and defender of Victorian family values. By the time of the COVID-19 pandemic in 2020–2022, Shakespeare’s loneliness seems to have lost its shame and embraces us all in its powerful consolation, but the preference for Sonnets read aloud by an actor on screen raises questions about the extent to which any voicing of the Sonnets mitigates their essential loneliness.