This chapter explores the concept of obscurity on social media platforms influences user's digital literacy, comfort levels, and experiences across age groups. By employing diverse methodologies to guide interface design, we investigate how obscurity introduces complexity, tension, and a sense of freedom for social media users. Highlighting obscurity’s impact as a barrier to meaningful online interaction, the study calls for “design evangelism” to cultivate inclusive, user-centred social media environments aimed at empowering the overall user experience.