Through an examination of how her tween son’s socially mediated life affects his educational perspectives, the author considers how this understanding informs and reforms current thinking about contemporary teaching and learning. In the age of social media and digital games, tweens are more engaged in what could be considered learning at home than they are in schools. What matters to the tween frames a new way of thinking about teaching and learning for both what these students need now and for their future work and learning practices. Emerging from this research are learning principles grounded in collaboration and communication in which tweens are contributors in all facets of teaching and learning.