Contemporary Indian English fiction has witnessed a significant transformation in its portrayal of love, relationships, and personal identity. Among the prominent writers of popular Indian fiction, Durjoy Datta occupies a unique position due to his realistic depiction of modern youth and their emotional experiences. His novels explore themes such as romance, heartbreak, self-discovery, family expectations, and psychological struggles within the context of rapidly changing Indian society. This paper examines the representation of modern relationships and emotional conflicts in selected novels of Durjoy Datta, including Of Course I Love You...! Till I Find Someone Better, The Boy Who Loved, The Boy with a Broken Heart, and Till the Last Breath. Employing a qualitative textual analysis, the study investigates how Datta portrays contemporary romantic relationships, emotional vulnerability, identity crises, and the tension between tradition and modernity. The findings reveal that his narratives reflect the complexities of urban youth culture, emphasising the challenges of commitment, communication, mental health, and personal aspirations. The paper argues that Datta’s works serve as important cultural texts that document the changing nature of relationships in twenty-first-century India.