The myriad cupids of Roman visual culture typically attract one of two responses: either they are seen as replicates of the god of love, Eros or Amor, or they fade into the background as ornamental bodies so banal that they preclude any focused attention at all. This dissertation offers a reconsideration of these figures. It suggests that one of the driving features behind cupids’ success is their ability to act as mediators – not just between lovers, or between divine and human realms, but also in a more straightforwardly visual sense: cupids are one of the most vital connective tools of the artist’s repertoire, used to link together different parts of an object or image surface, or to gesture outwards from the constructed environment of the artwork to the space of the viewer. As such, they are best understood not as isolated iconographic units but in relation to the surfaces, spaces, and other bodies on, in, or around which they are found. Cupids are not simply neutral units of visual syntax, however; they possess distinctive bodies which make significant demands on the viewer even before they are considered within wider contexts. Combining the divine, the infantile, the birdlike and the servile in one body, their behaviour is typically tactile, tender, caring, playful, and exploratory. I argue that the embedding of such tactile, mobile, marginal bodies within the built environment works to emphasise and inflect the viewers’ own sensory relations to their surroundings, calling into question the boundaries between image and ornament, touch and vision, viewer and viewed, and facilitating a more fluid and exploratory relationship between viewer and visual-material world. Ever responsive, cupid bodies can resonate in different ways depending on the medium and social context in which they are employed, and on the other bodies (real or represented, living or dead) which come within their orbit. In successive chapters, I focus on the cupids found on domestic and bathhouse mosaics from 2nd-5th century CE North Africa and Roman Syria, on sarcophagi from 2nd-3rd century Italy and Asia Minor, in a subset of 1st century CE Pompeian wall paintings and on a 1st century CE imperial temple. Focus on groups of objects in different media and from different time periods and geographic regions allows a sense both of the underlying stability of the figure type, and of the constellation of ways in which cupids can be manipulated by artists and patrons and understood by viewers in different settings. I look at their interrelations with the dominant bodies of these contexts – from the corpse interred within a sarcophagus to statues of emperors within an imperial temple – and at the ways in which they interact and contrast with other “ornamental” figures such as birds, gorgoneia, or nikes. In Chapter 4, I argue that the acts of mediation, support, and care performed by fantastical bodies can never be entirely separated from comparable acts performed by human actors, and reflect on the use of cupids to reinforce, or to transfigure beyond recognition, particular visions of power relations within a highly stratified social order. Cupids are pervasive and distinctive enough that no understanding of visual culture in the world of the Roman Empire can be complete without an understanding of their place in it. As well as offering reasons for the popularity of cupids per se, a more nuanced account of how these bodies work within larger object contexts contributes to ongoing discussions on the role of the sensory within Roman viewing, on the ways in which figural ornament shapes the lived environment of its human user-viewers, and on the representation of tenderness and interpersonal care in Roman culture.