Learning in caring contexts could be illustrated as an encounter between the scientific knowledge of caring and the learner’s lifeworld. This encounter needs a support that has the potential to bring caring science to life and to start an intertwining process with the lifeworld that creates embodied knowledge. The aim of this article is to illustrate the meaning of this encounter with help of a theoretical foundation and two examples of research projects with a reflective lifeworld research approach (RLR) founded on phenomenology. Both examples describe the student nurses’ perspective. One illustrates promoting learning through lifeworld-led supervision in pairs of students. The other illustrates learning environments that bridges the gap between theory and practice. These two examples show how the intertwining of caring science theory with lived experience required a certain learning and caring atmosphere that is open and sensitive for the lifeworld. In conclusion, lifeworld-led learning is more than learning per se. Lifeworld theory as a basis for supporting students’ learning could provide both a broadened and deepened understanding of the meaning of learning and also a greater understanding of how to support students’ learning.