Empathy is essential for designers to obtain a deep understanding of user experiences. It encompasses emotional and cognitive dimensions, combining the ability to resonate with others’ feelings emotionally, and to intellectually grasp their perspective, known respectively as affective and cognitive empathy. While empathy has been recognized as vital in a human-centered design process, empathic interactions with users depend on designers’ innate empathic tendencies, referred to as dispositional empathy, making the interactions prone to bias. This nuanced distinction between designers’ dispositional empathy and the resulting automatic responses to a context-specific user circumstance, known as situational empathy, remains underexplored. This research aims to establish the influence of designers’ dispositional empathy on the resulting situated outcome, thereby determining how empathy is triggered. Through an empirical evaluation using immersive virtual reality (VR) technology, participants embody the perspective of a user with vision impairment. This research reveals a statistically significant relationship between dispositional empathic concern and situational affective responses, and between situational cognitive and situational affective empathy. The findings highlight situational affective empathy as inherently linked to humans’ empathic tendencies, underscoring the significance of contextual elements to elicit cognitive empathy, and the potential for emotional responses to drive further cognitive thinking. Through a deepened understanding of empathy’s nuanced nature, the outcomes establish methods and tools for eliciting and measuring situational cognitive and affective empathy when experienced from a first-person perspective in VR. This research contributes to a broader understanding of the practical implications of constructing and experiencing VR experiences for enhanced designer empathy, facilitating future design innovation through digital contexts.