Arthur Schopenhauer (1788-1860) is one of the great philosophers in the world. He is a pessimistic philosopher who has his own special view toward life and the pleasures and pains of life. He is known as the philosopher of pessimism, as he articulated a worldview that challenges the value of existence. On the other hand, in the mystical and intellectual world of Islam, Mawlana Jalal al-Din, known as Rumi, (604-672 AH) stands. Unlike Schopenhauer, he is a ‘happy’ (optimistic) mystic. The importance of "blissfulness" and the ways to achieve it in life made us examine this issue comparatively in the thoughts of Rumi and Schopenhauer. With this aim, library resources were studied and necessary data were collected. The research method was descriptive-analytical. The results of the study showed that, unlike Schopenhauer, Rumi is a religious person and believes in God. This issue has created a significant difference in their definition of blissfulness and their hypotheses about the ways to achieve a blissful life. However, issues such as "who we are", "what we have", and "what we show" which Schopenhauer stated have an effect on the creation of happiness, and are similar to parts of Molavi's ideas. The interesting part is that, according to these two thinkers, the mental treatment of human beings with phenomena has an effect on feeling satisfied with life. ‘Who we are’ is a rich source of happiness. Rumi's and Schopenhauer's recommendations are still applicable to humans today since we are trapped in the machine and industrial world and are struggling with great sorrows.