With the advent of Web 2.0 technology and computers being used as tools for connecting people rather than for information processing, a new 'third' space is opening up that is redefining learning. Drawing on Sociocultural theory, Speaking to Learn traces groups of multicultural language learners as they negotiate their learning, asking the questions: What barriers prevent learners from investing in using another language? How can technology compound or respond to such tensions? The concepts of learning as dialogue-based and identity as dynamic, frame the nature of the historical, political, cultural and pedagogical factors influencing these learners. Their stories suggest the advantages of video-based web conferencing to learning and constructing more empowered identities. This identity construction is an important consideration for individuals from evolving democracies that are struggling to access international connections and recognition. The stories will be of interest to anyone involved in learning with computer technology, especially language learners, educators, researchers and policy makers as they consider the practices used and promoted in their language learning sites.