Although romantic and sexual relationships are an important aspect of young people's lives, research on how young people negotiate their love/sex relationships is lacking. New media environments provide a new context within which young people negotiate their love/sex relationships; however, what is negotiated is often not all that different from what was negotiated before the advent of new media technologies. Using an online discussion board and individual in-person interviews, this paper explores how young Australians, aged 18-25 years, engage with dominant gendered discourses to negotiate their love/sex relationships within the context of new media environments. Previous research suggests that young people make use of new media technologies to flirt with one another, to initiate new relationships, to maintain their relationships, and to fight and end their relationships. This paper focuses on young people's practices of mediated flirting, surveillance, and breaking up. It considers the creative and agentic ways young people use new media technologies in the negotiation of their love/sex relationships.