This article investigates the notion of happiness as presented in Mawlānā D̲j̲alāl al-Dīn Rūmī’s (d. 672/1273) Mathnawī-ī Ma’nawī, examining the intersection amid the scholarly discourse on the subject within the Sufi literature. Rather than a momentary sentiment, Rumi identifies happiness as the state of existence once experienced in the primordial realm. Having separated from the divine presence, the condition of human beings on earth would consist of pain and unhappiness. Since the worldly material is transitory, the happiness achieved through them is likewise. Therefore, Rumi encourages the individual to take a voluntary spiritual journey (sulūk) from the self (nafs) to the soul to be united with the divine (tawḥīd) to obtain celestial happiness once again, all while living in the terrestrial world (ʿālam al-s̲h̲ahāda)—the Mathnawī being a manual for the devotees on the path. This education provides an understanding for the individual of the nature of the objects, self-awareness, and divine enlightenment through the inner transformation of the self. Traversing through the stations and the states of the journey with the guidance of the spiritual master (murs̲h̲id), one purifies the ego (nafs) and eventually reaches the grade of contentment (riḍā). This stage signals the achievement of self-realization, wherein individuals grasp the divine spirit inherent in their existence and relish living in harmony with divine will, thereby, happiness. If the seeker reaches the state of self-annihilation (fanā‘), then the layers of nafs are completely unveiled (kas̲h̲f, leading to the gnosis (ma‘rifa). In this state, through celestial love, one begins to see Divine manifestations around them—placing true happiness as an intimate communion with the ultimate Truth (al-Ḥaḳḳ). This connection brings about a profound sense of genuine and celestial happiness. Through the Mathnawī’s elaborate narratives and poetic reflections, Rūmī encourages the reader to embark on a path of spiritual enlightenment. In contrast, happiness arises as the natural product of a life aligned with divine will, marked by a harmonious balance between the dual nature of human beings. This scholarly analysis highlights Rūmī’s significant contribution to the discourse on happiness within the Sufi tradition,h highlighting his contribution to the discourse within the Sufi literature and the enduring relevance of his teachings in our contemporary scholarly expedition for authentic gratification and the human condition.