Ekphrasis, the ancient practice of representing one art form within another, undergoes a radical transformation in the postmodern era. Moving beyond the Romantic ideal of harmonious synthesis or the modernist fascination with formal parallels, postmodern ekphrastic dialogues between poetry and painting embrace fragmentation, intertextuality, skepticism towards representation, and a critical interrogation of power structures embedded in both arts. This paper argues that postmodern ekphrasis is characterized by a dynamic, often destabilizing, dialogue that foregrounds the gap between word and image, challenges notions of artistic authority and authenticity, explores the materiality of both media, and frequently engages in socio-political critique. Analyzing key examples from poets like John Ashbery, Adrienne Rich, Lyn Hejinian, and Alice Notley alongside postmodern paintings, this study reveals how these encounters become sites of profound philosophical inquiry and cultural commentary, redefining the relationship between the sister arts for a fragmented age.