Foreign language learners purportedly demonstrate intercultural communicative competence in native speaker (NS) chat rooms through self-initiated negotiation sequences, including those triggered by pragmatic issues and cultural content. This study identified and classified one-to-one NS-learner negotiations between intermediate learners and NS of Italian in Web-based chat rooms. Classifications included (a) self-initiated negotiation moves (Shehadeh, 2001), such as questions concerning the target culture, and (b) indicators of skills of discovery and interaction required by the "intercultural speaker" in informal face-to-face contexts (Byram, 1997). The study also presents an intercultural model of negotiation that facilitates identifying cultural and pragmatic triggers by taking account of possible overlap with lexical triggers. The findings indicate that with minor pedagogical intervention, learner-initiated negotiation sequences are indeed a feature of one-to-one NS-learner chat interactions conducted in a noninstructed setting, with many learners actively seeking clarification on the target language and culture from their NS partners. In this way they avoid dysfunction and demonstrate intercultural communicative competence. These data have pedagogical implications for informal immersion experiences, such as residence abroad, for which learners are not always adequately prepared through standard classroom interaction patterns. They also suggest that negotiation strategies, as defined in this study, could be practiced before departure, with NS chat room experiences providing a form of virtual immersion and socialization experience in preparation for in-country "experience[s] of otherness" (Byram, 1997, p. 70).