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This paper applies an interactionist framework to examine the construction of heterosexual flirting via social media among teenagers. Using digital ethnographic methods, I demonstrate how the meaning of flirtation is encoded by the affordances of particular social media platforms. I found that digitally mediated flirtation operates in an “as if” paradigm of simultaneous ambiguity and yet clearly defined understandings. The vague nature of flirtation scripts allows teens to minimize risk for embarrassment and save face. Yet at the same time, commonly understood media ideologies and the spreadability of digitally mediated communication allows teens to reinforce and support each other’s definitions of flirtatious interactions. Interview data reveal heteronormative conceptions of online flirtation among teens. Further research is needed to investigate online courtship practices among LGBT youth. Despite predictions of early internet researchers about the identity-transcending potential of online interactions, gendered double standards still permeate teens’ romantic lives and sexual scripts such that girls are expected to be more passive and boys are expected to be more assertive. Although literature on adolescent sexuality, particularly in relation to social media, have been fraught with adult-imposed anxieties and moral panic, my research comes out of a child-centered framework that respects the agency and cultural constructions of teens. This paper raises questions about digitally mediated gender and sexual dynamics among teens at a crucial time when new norms and media ideologies are being formed and reproduced.