Background/Objectives: Pain is a complex and subjective experience influenced by psychological, cultural, and social factors. This study aims to investigate how social perceptions of pain affect the lived experiences and coping mechanisms of individuals suffering from pain. By comparing public discourse with the experiences of sufferers, we explore whether the social legitimacy of pain influences how it is managed. Methods: A multi-phase qualitative study was conducted, comprising eight focus groups with members of the Spanish general population and 19 in-depth interviews with individuals suffering from various types of pain. The focus groups explored social perceptions of pain’s legitimacy, while the interviews delved into the sufferers’ personal experiences. The data were analyzed using thematic analysis to identify patterns and disparities between public discourse and individual narratives. Results: The focus groups revealed widespread social empathy towards all types of pain. However, interviewees reported significant social pressure to normalize their behavior and downplay their pain. Many felt misunderstood, unsupported, and stigmatized, especially in environments where they held subordinate roles, such as the workplace or healthcare settings. Sufferers often resorted to silence or isolation to avoid judgment. Conclusions: While Spanish society outwardly legitimizes all forms of pain, sufferers experience significant discrepancies between public empathy and actual social support. The findings suggest that raising awareness alone is insufficient, and that structural changes are needed to address the daily burdens that individuals face when coping with pain, particularly in workplace and healthcare environments.