Like many rural regions, the East German rural district Altenburger Land suffers from outmigration, specifically by adolescents about to graduate from school, or shortly after graduation. Consequently, the age group 15–19 is under observation by local politicians seeking to increase adolescents’ attachment to “their” region in order not to lose the region’s youth and, thus, its future workforce. Simultaneously, youths are subject to widespread social communication patterns that stigmatize “staying” and urge adolescents to leave the region. The research on which this case study is based employed a mixed approach of expert interviews with policy-makers as well as focus groups and an in-depth interview with adolescents between 2013 and 2016. This was part of a larger endeavor to investigate how regionalized discourses of decline may impact life in the addressed regions. The specific part of our research detailed here aimed at illuminating the complex relationship between adolescents’ individual aspirations and normative institutional appeals observed in migration research. Interestingly, during focus groups, adolescents reproduced the same reasoning they had been subjected to by their peers, namely preferring to leave the region to start education or university studies. However in unison their answers seemed during focus groups, some adolescents revealed the true complexity of this decision and the related complex intra-family negotiations during more private conversations in smaller groups or in an one-on-one-interview. This study highlights the implications of different methods and settings for the researchers’ ability to access responders’ different registers of knowledge and emotions.