Discussions of technical and vocational education often concern various dichotomies that need to be bridged in learning. In this chapter, the dichotomizations between theory and practice, school and workplaces, and the what and how aspects of learning are addressed, and the chapter reports on and discusses some suggestions in research on bridging or handling such dichotomies in technical vocational education. Often, a holistic view and an integration of dichotomies are advocated. Bridging the gap involves complex processes, but being aware of the processes can be one step in the direction of integration. Another step, as argued in this chapter, is to abandon dualistic thinking and instead embrace pluralism, since research shows that there are often complex contexts involved that are not divisible into two different parts but rather into many different aspects. The complex processes of learning content in different contexts in vocational education constitute the students’ whole education. In order to understand these processes, it may be meaningful to divide phenomena into different units for analytical reasons, in order to understand how the parts integrate into the whole.