Facilitating democratic discourse, or people's ability to access factual information in service of thoughtful discussion of social issues, is critical for democracies to function properly. However, with the rise of online fake news, misinformation, and political extremism, it is becoming increasingly difficult to have civil conversations on the internet. As a first step to addressing this issue, scholars need to understand how the current design of online environments shapes people’s ability to respectfully engage across social and political differences. In this dissertation, I investigate how common social media design features, such as hashtags directly impact the quality of democratic discourse at-scale. Using natural language processing, statistics, and experimental design, I empirically demonstrate how linguistic behavior and the presence of political hashtags in online social media news articles impact the quality of discussions surrounding race, gender, and equality. Through my findings, I provide a theoretical examination of functionality and intertextuality as critical aspects of online design. Online design considerations that consider functionality alone tend to promote a digital public sphere that predominantly favors hashtag (or content) producers over non-users and passive content consumers. The sole emphasis on the functionality of design features drives frequency-driven research practices that prioritize discourse conditions for hashtag producers through volume-based definitions of discussion quality. Collectively, the research studies in this thesis are motivated by a desire to understand how online spaces can be better designed to foster interaction and discourse that can bridge rather than sharpen social differences. Results from this dissertation research strongly indicate that scholars, designers, and engineers need to rethink and evaluate how current methodological approaches that prioritize the functionality of online design choices are limiting the way we understand the quality of democratic discourse on the internet. As a step towards this direction, I evoke Kristeva’s notion of intertextuality to demonstrate how online design choices facilitate the power of language in which important social topics are discussed across networks.