In recent years, much progress has been made towards elucidating the function of ekphrasis in Roman epistolography, especially with relation to the writings of Seneca and Pliny. Following on from these precedents, this article mines the epistles of three prominent Roman letter-writers, Cicero, Horace, and Ovid, for their intermedial elements. The motifs of oral quotations, handwriting, and human tear stains, which interweave the sources analysed, are shown not only to straddle the borders between distinct media, but also to engage with multiple senses as a result of their multiple medialities. Oral quotations integrate speech into written texts and thus necessitate both sight and hearing. Handwriting likewise consists of both a ‘basic mediality’ – the visual – and a ‘qualified mediality’ of chirographic distinctiveness, and thus necessitates not only perception via sight but also recognition. Tear stains, which range from the actual smudges in Cicero’s missives to metaphorical ones in Tears don’t feature in Horace’s letters. Ovid’s epistles, are in turn geared both towards sight and touch, since they simultaneously alter the letter’s appearance and surface. However, these intermedial connections have different effects in prose and poetry epistles: they enable the former to transcend the very category of ‘letter’, but confine the latter within the epistolary genre by characterising them in material terms.