On Love & Data develops a dialogue with hierarchies embedded within machine learning and AI architecture and one's individual agency in transforming the algorithms within it. Many algorithmic technologies are rooted in methods that limit and cajole information from the first human and computational assumptions. We assess ourselves using false dichotomies that force inadequate choices building a world bereft of complexity and nuance.The disinclinations of our systems to cope with the unseen, the unknown, difference, and change limit possibilities for everyone. Through intelligent technologies – the ones that look like us, the ones that serve us, and the ones that do neither – we have the ability to understand and organize human activity with complexity and broadly principled care. So, why aren’t these the goals of our algorithmic doppelgangers, assistants, and technological ecosystems more generally?