The notion of identity is one’s subjective position in the society. It is the social representation adopted by an individual, occurring at different levels (e.g. cultural), (re)produced and practiced semiotically, for example, through language. With the emergence of contemporary dating apps, individuals have a new way of building up their interpersonal relationship, particularly in their dating life. Users of dating apps write up a short profile that best introduces themselves while registering. People vary significantly in terms of their language, and the variation in their language reflects how they wish to represent themselves in front of their potential dates. Singapore is a sociolinguistically heterogenous country with both Asian and Western social and cultural norms. Heterosexuality and masculinity have been deeply embedded in this country, largely invoked by its National Service (NS) act. Under this unique context, this study seeks to understand the semiotic relation between language and gender, with a focus on the social representation of masculinity among Singaporean heterosexual men on dating apps. Using corpus-driven and critical discourse analysis methods, this study finds that the masculinity of Singaporean heterosexual men is contrastively represented through language. Evidence is obtained from the discourse data collected from the written profiles of those active dating app users. Singaporean heterosexual men’s devalued self-recognition is contradicted by their ‘mental fitness’ – a positive self-objectification of their bodily masculinity and active physical fitness – deeply influenced by the country’s embedded national rituals. Additionally, the study finds evidence of linguistic eagerness in them navigating conversations with the opposite gender, contrasting with the covert expression of their sexual desire in discourse. The study argues that the complex and multifaceted nature of masculinity among Singaporean heterosexual men is reflected in their use of language on dating apps, highlighting the importance of language in the social construction of gender identity.