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Purpose High self-awareness can promote communication and empathy. The Enneagram is a well-known personality tool to enhance self-awareness. We evaluated differences in empathy among medical students using the Enneagram typology. Methods This cross-sectional study included first and second grade students at the Inje University College of Medicine. The Jefferson Scale of Empathy was used to measure empathy and the Korean Enneagram Personality Type Indicator was used for examining personality characteristics. Empathy scores were analyzed according to the Triads, Hornevian group, Harmonic group, and each Enneagram type. Results The Instinctive triad, the Withdrawns, and the Positive outlook group were the most common, and the Feeling triad, the Assertives, and the Emotional realness group were the least common. Students in the Feeling triad and the Dutifuls had higher compassionate care (CC) scores as compared to their counterparts. Type 2 and 6 students showed the two highest empathy and CC scores. The empathy score of type 3 students was the lowest. Type 7 had the lowest CC score but the highest perspective taking score. Conclusion These differences in empathy according to Enneagram personality types can be applied to medical education to maintain and improve medical students’ empathy.