The present study aimed at comparing student teachers’ and medical students’ experiences of emotionally challenging situations during workplace education. Eight group interviews were conducted and data analyzed with a thematic content analysis. Findings suggest that both student groups meet similar challenges of experiencing various situations that are emotionally difficult. In order to manage these experiences, students are involved in processes of drawing boundaries. To manage emotions of strong compassion, or coming to close, students realize that they need to draw boundaries between the professional and the personal life. Students also draw boundaries to uphold their view of the professional role, to protect against influence from negative role models and a non-compassionate professional culture.