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We are interested in understanding the individual and environmental attributes that contribute to a youth’s sense of connection. Specifically, we explore the ways in which close relationships with nonparental adults (such as teachers, coaches, mentors) are 1 vector of connection through which PYD occurs. We focus on interview transcripts from 37 youth, ranging in age from 11 to 18 years. We look across their narratives of relationships with adults in their lives as well as analyze these narratives in conjunction with individual level characteristics derived from survey data. Several themes across these close relationships were identified as facilitating or impeding connection including: adult personality characteristics, shared interests, and length of time spent together. Role expectations and role boundaries were also defining features in the narratives of YARs. We suggest that context of YARs is an important factor in understanding the nature of the relationship and youth perceptions of adults, in general. Finally, we offer suggestions for conceptual clarity and the importance of using qualitative methods for understanding connection.