Background/Context: Digital media seem to pervade all aspects of American youth's lives, from communicating with friends and family to learning about the world around them. Many educators and scholars celebrate the new opportunities for learning that Web 2.0 tools present, and empirical evidence suggests that computer-mediated communication positively influences the quality of adolescents' friendships. Yet, adults are also mindful of the risks associated with youth's digital media activities, including the negative effects of multitasking and the implications for identity development of being perpetually "tethered" to one's friends and family. Focus of Study: Because widespread Internet and mobile phone use are still relatively new phenomena, further research is needed to investigate their effects on young people. Existing research indicates that the effects are unlikely to be wholly positive or negative. In this article, the author explores the tension between the promises and perils associated with digital media in the context of one college student's daily experiences. Research Design: Using the qualitative method of portraiture, the author examined how one college student uses digital media in her everyday life; her motivations and goals for using various media; and the opportunities and drawbacks she perceives in her daily media use. Conclusions: This student's experiences illuminate the always connected, always connecting quality of life for today's young people. Her experiences also reveal the complexity of life with digital media, because media both support her connections to people and ideas and give rise to feelings of disconnection and fragmentation. Finally, this portrait highlights the need for and value of nurturing youth's reflective practices and providing them with spaces to engage in sustained reflection.