This sociolinguistic and interdisciplinary work critically looks at the social construction of multilingualism, ethnicity, and citizenship, specifically through the voices of nine self-identified multi-generational Italian Canadian youth participating in French language learning and teacher education programs in the Greater Toronto Area. While considering present-day discourses on pluralism and trans-nationalism, I explore how the youth socially construe their identities and invest in ideologies and representations of language learning in an urban globalized world. In doing so, I highlight the different conceptions of what being Italian Canadian, multilingual and multicultural means to these youth and the ways in which they position themselves vis-à-vis the acquisition of French as an official language. One significant contribution of this work is its call for a more multi-dimensional and symbolic conceptualization of the notion of investment than that purported by Norton Pierce (1993, 2000). Drawing upon an ethnographic approach, reflexivity, and discourse analysis (Fairclough, 1995) of both audio and video/film recorded interviews, observations, and focus groups (collected within multiple discursive sites), I demonstrate how some of the participants' lived social and linguistic practices problematize social categories, illustrating the multiple voices, exercises of agency, and shifting, complex positions of the youth as they manage, negotiate, and challenge discourses of language, power, and representation. While my findings underscore different language learning experiences as well as the different dimensions of constraints, opportunities, conditions, and outcomes in the attainment, continued investment, and maintenance of symbolic and material resources, they also shed light on the processes of inclusion and exclusion by looking at who gets to define what is the 'right' kind of multilingualism, in which discursive spaces, and who can claim the 'right' forms of cultural and linguistic capital (Bourdieu, 1982; Byrd Clark, 2007; Heller & Labrie, 2003) to be considered a multilingual and multicultural Canadian in the new globalized economy. Lastly, this work creates social spaces for overlapping identities, which could possibly challenge the status quo, crossing social borders in Canada and beyond. This doctoral dissertation has implications for all those involved in multilingual and multicultural education, language planning and policy and immigration studies.