This article aims to understand Leopold Bloom’s masochistic tendency as a way to the purgative recovery from the domestic catastrophe and social alienation in Ulysses (1922). Masochism which was derived from an eponymous Austrian author Leopold von Saher-Masoch. This term refers to a peculiar practice in seeking of physical pain or humiliation. Bloom’s self-affliction culminates with his connivance at his wife’s adultery plan. This masochistic plot is recurrent throughout a day, namely Bloom’s day. Meantime, in reality, Bloom is desperate to stay in equanimity despite the catastrophic event at home. However his desperation, to be strange, evokes indefinable empathy and sympathy. Given that most people abhors the unusual preference, it’s strange enough. This paper sees that Bloom’s Catharsis-purgative recovery from the pending anxieties is pivotal in this emotional sharing, albeit how weird he looks. Additionally, the literal meaning of adulteration, being impured, enhances the analogical relationship between two themes: adulteration and purification. That is, Bloom’s psychological trauma is a self-begotten misery; but it functions as a purgative device to relieve that autochthonic injury in turn.