Love can be understood as a “bottom-up” doing, i.e., loving, imminent in our psyches and enacted in embodied practices. Mystic poets, in seeming contradiction, sometimes treat love as a transcendent mode of being that exists in, of, and for itself. It is grace bestowed “from above” that connects those blessed to a sacred realm of existence beyond the phenomenal world. Grounded in contemporary psychology yet heavily inspired by bhakti poetry, song, and hagiography in this perspective essay a worldly understanding of love is mirrored against and then harmonized with a transcendent innerstanding of love. Love as simultaneously embodied and transcendent is then linked to the interrelated themes of culture and leadership. We need loving guidance to grow-up into mature adults. As we then learn to generate love ourselves, we can guide others and share love in an effortless savoir-vivre of ingrained cultural practice. “Cultures of love” so envisaged thus need the guardianship of healthily matured leaders. Unfortunately, in our turnabout culture of ego pomp codependency masquerading as love is taken for the real thing. Love gurus’ personality cults blossom in such regressive environments. In contrast to a fixing of inner emptiness in codependent push-and-pulls between leader and follower, mature loving is expressed in mutual celebration of inner overflow and personhood. From this point of view, leadership is synonymous with servanthood. Such leadership foregoes the quest for power and control. It knows no other motive but the radical acceptance of Other as part of Self to form a new unity. This new unity is the Culture of Love here envisaged.