This article compares traditional offline flirting with cyber-flirting. We begin by providing a definition of offline flirting, which we follow up with our own elaboration of cyber-flirting. The article then draws from psychoanalytic theory, in particular Winnicott's object-relations theory, to propose that cyber-flirting can be a form of play. While this is not an empirical study, we do attempt to present a theoretical framework for the conception of cyberspace. In presenting this framework, we draw from past qualitative and quantitative studies on Internet relationships. We emphasise the problems with past researchers' obsessive attention to the absence of the body online, and suggest that new theorising on Internet relationships needs to consider how the body is re-constructed. We propose that cyberspace can be what Winnicott would describe as a "potential space" for play, and this particularly applies to online spaces, such as MUDs, MOOs and Chat Rooms. In addition, we suggest that cyberflirting may promote psychological growth, but it may also become a destructive and exploitative behaviour directed towards 'others'. We conclude this paper by pointing out the therapeutic implications of considering cyber-flirting as a form of play. It is intended that this paper may assist our conceptualisation of this under researched area of cyber-interactions. (Bakhtin -cited in Green, 2001, p.159)