This thesis explores the relationships and experiences that young adults have with and within complicated and always changing new media environments, such as those afforded by social media platforms and mobile media applications. By analyzing the ways in which digital realms are both open and interconnected and also marketized and restricted, this thesis explores how a contemplative approach to new media literacy pedagogy could help young adults to perceive new media from multiple, contradictory viewpoints at once, thereby supporting them in creating healthy, productive, creative, and imaginative relationships with the digital and public technologies mediating their lives, at the same time mitigating the challenges associated with commercialized, habituated new media experience. This thesis takes an auto-ethnographic approach, merging personal narratives with qualitative interpretations of where philosophies of technology, theories of media literacies, and the results of focus group studies intersect.