What did friendship mean in the shifty landscape of politics in medieval India? This article seeks to answer this question by looking at the illustrative animal stories of the Sanskrit anthology Hitopadeśa (800–950 CE). As a text belonging to the nīti genre, the Hitopadeśa emulates the Pañcatantra (300 CE) and reiterates the following significant thought in Indian political wisdom: As an affective relationship, friendship provides a vital ground for the political and ethical progress of an individual. It also conveys that precisely because of its emotional content, friendship can also turn into a source of deception and treachery. We will see how the animals appearing in the Hitopadeśa act as perfect metaphors for individuals who must find a balance between their natural dispositions and cultivated aspirations as they navigate the terrain of friendship. We will also read about the diverse markers of friendship as well as the circumstances under which strangers become friends and friends become enemies. Above all, we will explore the rich ambivalence in the stories and the poignant message that the interlocutors of the theories of friendship can be as unpredictable as friendship itself.