Background: Considering the widespread use of personal protective equipment (PPE) during the COVID-19 pandemic, which conceals facial expressions, this study aims (1) to explore facial expression recognition ability; (2) to assess the ability to read facial expressions under different conditions of face coverage; and (3) to investigate the role of emotional intelligence in facial expression recognition. This multidimensional exploration provides vital insights for creating novel learning methods, emphasizing the pivotal role of emotions. Methods: The study sample comprised 124 Italian adult subjects, consisting of 71 females (57.3%) and 53 males (42.7%), with a mean age of 35.31 years. The present investigation employed the Emotional Intelligence Scale (EIS) and an image-based questionnaire administered via the online platform Google Forms. Student’s t-test and one-way ANOVA were computed with SPSS (v. 29). Results: Significant differences were found based on gender, profession, and level of education in face expression recognition and emotional intelligence. The implications for learning processes are discussed. Conclusion: This study unveils the intricate dynamics of emotion recognition, gender, occupation, level of education’s influence, and emotional intelligence. By incorporating these insights into educational programs, a transformative process can be initiated, nurturing not only empathy, cultural insight, and emotional intelligence but also catalyzing the evolution toward inclusive and emotionally equipped societies.