Teachers’ past learning experiences, also referred to as “apprenticeship of observation,” can affect their beliefs and, in turn, their teaching practices. This study focused on the apprenticeships of observation of Chilean novice English teachers and sought to identify the possible influence of their past English teachers on their teaching and learning views in an English as a foreign language context. The qualitative multiple case study design gathered the narratives of 18 teachers using an open-ended survey and in-depth interviews. Results showed that the teachers’ apprenticeship of observation influenced their socio-emotional and affective views on teaching with a main concern on teacher-student relationships. From a sociocultural perspective, it was found that feelings associated with these experiences helped them understand their own practice.