The literary pieces that this paper aims to analyze, Yusuf Al-Sibai's novel The Water-Carrier is Dead (1959) and Yasunari Kawabata's autobiographical short story The Master of Funerals (1922), both have male characters traversing intractable grief, loss and fear of death as their protagonists. Despite significant differences in social, cultural and religious backgrounds, the two novelists share one concept – the problematisation of coping with undesirable emotions subsequent to death and significant losses.  Each one of the two works is a poignant tale suffused with grief and bereavement and each focuses on the dilemma of a bereaved male protagonist suffering considerable loss(s). The principal concern of this paper is to offer an analysis of the two bereaved protagonists' attempts to traverse grief, loss and fear of death in their particular circumstances as depicted in the two pieces under consideration. The two central characters, Shousha and Kawabata, will be compared and contrasted in terms of how they traverse and even master their difficult emotions and reach desensitization to death. Other questions concerning their disposition, their negative attitude towards death and inability to forget traumatic memories and control undesirable emotional responses will be raised and answered in order to emphasize the difficulties the two protagonists meet during their traversal (the journey from supersensitivity to desensitization).