In today's sociocultural milieu, characterized by pervasive social media and evolving conceptions of masculinity, this study examines the interplay among loneliness, social media addiction, self-reliance, and life satisfaction across Generations (Gen) X, Y, and Z. Employing a comprehensive model, the study explores social media addiction as a mediator between loneliness and life satisfaction, with a focus on the moderating role of the pivotal masculine trait of self-reliance in the loneliness-social media addiction relationship. Based on an online survey of 775 Israeli men aged 18-58, the findings reveal unique generational patterns. For Gen X, social media addiction negatively correlates with life satisfaction, without mediation or moderation effects. In Gen Y, loneliness is directly associated with life satisfaction, and a positive correlation exists between loneliness and social media addiction. Notably, self-reliance moderates the link between loneliness and social media addiction, amplifying this association at lower self-reliance levels. Gen Z replicates the Gen Y findings albeit without the moderation effect. This study contributes nuanced insights into the literature on masculinity, revealing the evolving nature of self-reliance-a crucial masculine trait-across generations. Such evolution, in turn, is associated with responses to loneliness and patterns of engagement with social media.