Purpose/Objectives Empathetic communication of dentists with their patients is a primary characteristic of their health care. This study aims to evaluate dental students’ empathy levels during the transitional period of internship and postgraduate studies of different specialties at one of the oldest dental schools in Saudi Arabia and explore how this empathy was affected by gender, age, and study duration. Methods In this study, the self‐reported empathy level among the participants was assessed using the Jefferson scale of empathy‐student version (JSE‐HPS). This survey includes a 20‐question Likert scale formulated to measure clinical empathy in health care professionals. The JSE‐HPS was distributed to all registered dental interns and postgraduate students during the academic year 2019–20 in King Abdulaziz University Faculty of Dentistry (KAUFD), Jeddah, Saudi Arabia. Results Mean total score of empathy of the participants was (101.07 ± 14.8) with a response rate of 89%. A statistically significant higher empathy score appeared among dental postgraduate students in general (p = 0.04) and specifically among the females (p = 0.04) and those with postgraduate programs for more than four years, (p = 0.02). Dental postgraduate students scored significantly higher in the parameters of standing in patients’ shoes (p = 0.02). Conclusion Gender, academic level, and duration of postgraduates' studies influenced empathy more than the age of the dental graduates in KAUFD. Our recommendation is to integrate empathy into the dental curriculum emphasizing interactive communication skills and early patient contact.