Three half-hour conversations each from five English and four Spanish dating chat rooms were analyzed following conversation analytic methodologies. Participants in the chats often engaged in playful and humorous erotic conversations, using a set of interactionally negotiated conventions about chatting that constitute a play frame, characterized linguistically by graphemic representations of laughter, appropriations, reproduction of a humorous pronunciation, and interactions through alter personae. Such playfulness enhances participants' pleasure while allowing them to maintain critical distance, and balances the constraints of public interaction with the pursuit of private erotic pleasures. This study contributes to our understanding of the social and discursive dimension of sexuality, going beyond issues of sexual identity and focusing on the conversational negotiation of eroticism and desire.