Older adults often struggle to adjust to the rapid changes in the digitizing media landscape. In this article, we study, first, how 10 older adults adapt new online media into their daily lives and, by doing so, adjust to the changing "rules of engagement" that guide online-media use in their social surroundings. Second, we analyze how this adaptation process generates change in older adults' social connectedness. Results suggest that older adults' non-use of popular online media results in social exclusion. Enhancing their social connectedness, requires older adults to (partially) conform to new communication norms and values. Based on our findings, we propose three adaptation strategies that enhance both offline and online social connectedness.