The COVID-19 pandemic and the subsequent lockdown measures in many countries have increased young people's engagement with digital media. The digital divide goes beyond just having devices and includes differences in how well young people can use digital technology. In this paper, we shift our attention beyond screen time to the nature of the adolescents' digital media use. Our study looks at two adolescents from different backgrounds to understand how their digital media experiences differ in viewing, play, and reading. We add to the literature on the influence SES has on the ways in which adolescents are using digital media during the COVID-19 pandemic in Singapore. Our study was conducted during the pandemic and participants were selected using convenience stratified sampling and the snowballing method. Our findings show that the adolescents' digital viewing was motivated by the need to be a part of an affinity group and that while the viewing was passive, it served a social function to develop a sense of connectedness with peers. We also found that adolescents from high socioeconomic backgrounds tended to engage in more digital reading compared to their peers from low socioeconomic backgrounds. In addition, while the adolescents' digital play was shaped by their socioeconomic realities, they were able to make the most from their circumstances and demonstrated both creativity and savviness. By demonstrating the disparities in digital media experiences between two adolescents from contrastive socioeconomic backgrounds, we shed light on the implications of the digital divide, where both equitable access to digital resources and the development of digital literacies necessary to navigate the digital landscape is currently lacking. We argue for the importance for researchers and policymakers to move beyond acknowledging long-standing concerns and take actionable steps to address these issues.