This paper examines the acculturation process of male Central American-origin youths in Toronto, a group who are known to have a higher than average risk of dropping out of high school. Using data from semi-structured interviews with a small sample of male youths born in the region or born in Canada to parents from the region, we examine interrelated and shifting friendship patterns, ethno-social identities, and aspirations for schooling. The findings reveal that some youths become marginalized with weak friendship networks, diffuse ethno-social identities and low school completion aspirations, while others develop relatively strong affiliations exclusively with co-ethnic friends who have modest school completion goals. The strongest trend was toward being integrated with a mix of co-ethnic friends and those from other backgrounds, hybrid ethno-social identities, and higher schooling goals. The analysis examines whether the youths are aware of the relationships between social belonging and academic belonging, and whether they feel it possible to escape from being “boxed in” to acculturation patterns associated with poor school completion. These findings add to research on efforts to understand and improve schooling outcomes for “at risk” minority youth in a multicultural city.