Contemporary use of double modals (DMs) is mainly associated with Southern American English dialects. However, they originated in British English (Fennel, 1993; Montgomery & Nagle, 1993), and their rise dates back to Early Modern English (Nagle, 1994). Existing research on DMs also suggests that they are mostly used in trade interactions, while negotiating one’s needs and wishes (Mishoe & Montgomery, 1994). This paper presents a study which takes a diachronic approach and investigates contexts of DMs’ use in the earliest years of their attested existence. The analysis considers a selection of metadata as well as in-text data retrieved from the Early English Books Online corpus; a collection that includes texts from the Early Modern English period. The investigation looks particularly at: the chronology of DMs’ use, their geographical distribution (with the authors’ origin and place of publication taken into account separately), as well as the characteristics of the circumstances in which literary texts document them.