Recent investigations into the UK National Health Service revealed doctors' failures to act with compassion and professionalism towards patients. The British media asked questions about what happens to students during their learning that influences such behaviour as doctors. We listened to 200 medical students' narratives of professionalism dilemmas during workplace learning (n = 833) to understand the range of dilemmas experienced and emotional reactions to them. 32 group and 22 individual interviews were held across three medical schools (England, Wales, Australia). Data were analysed thematically (Framework Analysis), for negative emotional content (Linguistic Inquiry and Word Count) and a narrative analysis of one exemplar narrative was also conducted. While a wider range of professionalism dilemmas than previously identified were found, most were classified to five main sub-themes. Within these sub-themes, clinical students' narratives contained more negative emotion words than pre-clinical students' narratives (p = 0.046, r = -0.36). Narratives of 'patient safety and dignity breaches by students' contained fewer anger words (p = 0.003, r = -0.51), 'patient safety and dignity breaches by healthcare professionals' contained more anger words (p = 0.042, r = -0.37), 'identity' narratives contained fewer anxiety words (p = 0.034, r = 0.38), and 'abuse' narratives contained more sadness words (p = 0.013, r = -0.47). The narrative analysis revealed a complex interplay between identities, attribution of blame, narrated emotions and emotional residue. Analysing emotional talk within narratives suggests that medical students sometimes struggle with contradictory formal and informal learning experiences around professionalism arising from a cultural clash. We provide educational recommendations to facilitate students' coping with their emotional reactions to professionalism dilemmas and to facilitate cultural change.