Wheelchair users, as a minority group in the society, often face a lack of understanding of their physical, emotional, and social challenges. This empathy gap leads to miscommunication, misunderstanding, and exclusion in social interactions. This study evaluates the empathy gap in help-related social challenges for wheelchair users and investigates the effectiveness of an AI mediator, facilitating social interactions through communication by incorporating politeness strategies, through a video-based simulation experiment. The results provide insights into implementing appropriate politeness strategies in communication and demonstrate the efficacy of the system in promoting positive interactions to address the challenges wheelchair users facing. The findings contribute to development of future smart wheelchairs to improve mutual understanding and cooperation between wheelchair users and others, promoting positive interactions and a more inclusive society.