This research article explores the portrayal of masculinity in Howard Jacobson’s novel, The Finkler Question, through a postmodern lens. It examines how the novel challenges traditional beliefs about masculinity and male identity, drawing on Jean-Francois Lyotard and Judith Butler to explore the fluid and contested nature of masculinity. Using textual analysis, the study focuses on themes of ageing, sexuality, and power in the portrayal of male characters and their relationships. The findings reveal that these characters navigate complex and contradictory identities, challenging conventional notions of masculinity. The novel critically reflects the socio-political context of contemporary Europe, highlighting diverse expressions of masculinity and the impact of societal expectations and traditional gender roles on male identity. Through its characters, the novel envisions a more inclusive and diverse understanding of male identity, emphasizing the fluid and evolving nature of masculinity. This study contributes to the ongoing discussion on gender and identity by demonstrating how The Finkler Question provides valuable insights into the nuanced nature of masculinity in contemporary Europe. The novel's critique of traditional masculinity underscores the need for a more inclusive understanding of male identity and highlights the importance of a postmodern perspective in grasping the fluid nature of masculinity in modern society.