Sustainable development is a matter of truth and love. A transition from unsustainable to sustainable culture(s) will fail if both aspects are not lived – and mentioned in theory and practice of personal sustainability. Starting from a very human and everyday perspective on the connections of truth, fear and love to sustainable development, in the second part of the chapter they are put in the context of human history and the evolution of consciousness. How we deal with the world is an expression of our relatedness to the world. Recurring to a typology of human-world-relationships categorically different qualities of human relations to the world are shown. The appearance of “sustainable development” is a clear hint for a (collective) dawning shift to a new type of relationship: from an “I-It” to an “I-We” relation. An essential aspect of an I-We relation to the world is the awareness of being part of the world and our respectful bond with it (“love”) – without abandoning the distance of an I-It relation (“truth”) that provides us with knowledge. Finally, the transition to a culture of sustainability would mean a categorical new quality of life and being human – and a unique step in the history of mankind.