To empirically investigate language learning in relational and cultural settings, the authors developed and administered the Ecological Language Learning and Academic Success scale to an ethnically diverse sample of 269 urban high school students who speak a language other than English at home. Exploratory factor analysis revealed a four-factor structure (Educational Learning, Friend-Based Learning, Family-Based Learning, and Community-Based Learning) with strong reliability estimates. To explore the interrelationships across the various ecological settings, the authors then conducted multidimensional scaling to create a visual representation of the distances between scale items in three-dimensional space.Their findings reveal a disconnect among the various settings. The authors discuss these findings in the context of maximizing bilingual students' cultural assets by bridging the social communities in which they learn English and achieve academically. (Contains 1 figure, 3 tables and 1 note.)