The aim of this study was to describe how supervisors’ support nursing students learning in pairs, during their clinical practice. The research is based on a Reflective Lifeworld Research approach founded in phenomenology. The analysis is based on seven individual interviews with head supervisors and four group interviews with base supervisors at Developing and Learning Care Units. There is a total of eleven Developing and Care Units in both somatic and psychiatric care. This learning environment is designed to integrate theory and practice through lifeworld didactics in order to support pairs of students in their professional development. The results show that supporting students’ learning in pairs is based on interpersonal meetings and entails focusing on learning in pairs, where both each individual student and the pair of students as a unit are given space. Being the ultimate support for students’ learning is a major challenge that requires flexibility towards the pair of students. Supporting students’ learning is also characterized by being present for the students with a reflective supervising approach, at the same time as supporting means to take a step back in relation to not be too prominent. The learning support, which is characterized by structure and reflection, is also challenged by the competing “reality of the nursing situation”, which is shown in a balancing act between the demands of the “reality of the nursing situation” and the space needed for reflective learning.