Fans of contemporary U.S. teen drama television series often feel that their pleasures are devalued. They face derision from people in their lives (for example, partners, friends, and family members), in public and popular discourses, and also within fan spaces. Such derisions come from longstanding and negative perceptions of soap opera fans, and other feminised popular cultures and behaviours. An established body of feminist and fan studies research is dedicated to taking fans’ pleasures in such texts seriously, since feminist scholars ‘turned to pleasure’ in the 1980s. Yet the rise of social media platforms in the mid-2000s warrants a return to questions about fan pleasure and gender, given the centrality of digital technologies to contemporary teen drama fandoms, their ubiquity in everyday life, and the enduring stigmatisation of youthful and feminised media cultures. This thesis offers an examination of teen drama fans’ negotiations of their (guilty) pleasures. It focuses on the ways fans navigate the relationship between cultural derision, guilt, and pleasure, and examines the role that social media technologies and their associated discourses play in this complex dynamic: one that is unique to a social media age. My project uses a combination of in-depth interviews and social media observation data to engage with twenty-two fans of three contemporary U.S. teen drama series: Pretty Little Liars (2010-2017), Revenge (2011-2015), and The Vampire Diaries (2009-2017), and makes four original contributions to knowledge. I (1) explore how adult fans’ reproduction of what I call a quadruple devaluation (age, social class, gender, and sexual orientation) is intrinsic to their pleasures, (2) show how the various discourses of digital technologies – privacy, participation, and labour – are central to fans’ experiences of pleasure, (3) argue that fans disembed, or detach from some of the logics of social media platforms to facilitate secrecy, and (4) conclude by pointing to new relations between guilt and pleasure, arguing that guilt and pleasure (and derision) work together, because to have pleasure without guilt seems beyond reach for my respondents, especially for women. This thesis intervenes in established debates about fan pleasures and feminised popular cultures, offering an exploration of teen drama fandom and forging a dialogue between research on teen drama fandom, (post)feminism, and social media.