To question hegemonic versions of South Asian mythology, popular culture offers multiple opportunities by analyzing gender and power dynamics from different angles. In particular for goddess myths, there is no dearth of material to study the intersections of gender and caste oppression. But what about demonesses or Rākṣasīs? One popular misogynic story type that survives in modern reworkings involves shape-shifting demonesses cast as femmes fatales of the man-eater type. One such recent, comedy-horror feature, Amar Kaushik’s 2018 Stree, was popular enough to inspire a sequel, Stree 2. The story type itself and its related anxieties are old, documented already in the classical epics, where Rākṣasas in general are portrayed as outside the pale of civilized society by the elite authors, who refer to themselves as “Aryan.” Scenarios of Rākṣasīs proposing love marriage to epic heroes who counter with deep ambivalence are found in mirroring cases in the Rāmāyaṇa and in the Mahābhārata. In the former, none less than Rāvana’s sister Shūrpanakhā propositions Rāma (and Lakshmana) without success, whereas in the latter, the demon Hiḍimba’s sister, Hiḍimbā, marries one of the Pāṇḍava brothers, Bhima. The Hiḍimbā episode is particularly interesting as a potentially successful “interethnic” partnership between an “Aryan” hero and a “tribal” woman. This chapter studies on what is at stake in “marrying the demoness” in the classical as compared to multiple contemporary Hiḍimbā-episode retellings from diverse perspectives. The analysis focuses on how story tellers mobilize emotions in subtle ways to validate or discredit the marital union.