This chapter provides insight through personal narrative into why Caring Science forms the underpinnings of author’s professional and personal life, it shows specific elements of Caring Science that strongly relate to teaching, learning, and interacting in the digital world and also shows how the author’s work in online caring is guided by Caring Science. Strong trends in nursing education indicated that online instruction was quickly becoming a standard method of delivering nursing education. Massive open online courses (MOOCs) are administered through universities or organizations that possess the educational infrastructure to host and manage large-scale online courses and trainings. Dialogue about how MOOCs can best be utilized to provide educational opportunities at local, national, and global levels, while still preserving traditional educational programs/institutions, is ongoing. Free and open digital gatherings transcend geography, economic limitations, and sociopolitical conditions that would otherwise not allow for the development of significant connections, interactions, and collaborations.