This paper focuses on the relationship between gender and language in James Joyce’s Ulysses and presidential debate speeches. Language and its utilization can provide valuable information about individuals—I seek to explore what language conveys through a gendered lens. I use Linguistic Inquiry and Word Count (LIWC2015) statistical software to further analyze the relationship between gender and language. LIWC is a text analysis application that captures emotional, cognitive, and structural components of a text. I use LIWC’s linguistic dimensions, grammar, and psychological processes functions to research a potential relationship between linguistics and perceived gender identity. Although literary analysis has the potential to provide rich insight into texts, statistical analysis offers a unique perspective that may be difficult to characterize otherwise. My research is unique—text as data research captures human communication and interaction; the use of LIWC software will enable me to explore a niche space of research intersected with literature, and add to existing canons in this particular area. Through analyzing gender and language through statistical and critical literary means, I deconstruct the relationship between language and gender perception.