Circularity seems to be on the tip of everyone's tongue and, interestingly, eastern European care workers and Italian employers are starting to depict this arrangement as their “ideal.” Yet these idealized descriptions still raise a number of questions. Throughout this article, the narratives from eastern European “circular-carers” and those of Italian employers illustrate the way commodification of care, transformation of gender roles in post-Soviet countries, and the precarization of women's labor (especially for breadwinners age 50 and older) influence individual desires and decisions and, thus, promote the spread of this migratory pattern.