The aim of this study was to explore adolescent dating relationships through the prism of high school girls' narratives. We probed the contexts and meanings associated with different forms of dating to better understand the developmental significance of romantic relationships during adolescence. Cross-sectional, in-depth semi-structured interviews were conducted with 20 high school females. The analytic approach was phenomenological and grounded in the narratives rather than based on an a priori theoretical framework. Interviews were digitally recorded, transcribed verbatim by research staff and entered into ATLAS.ti 6, a qualitative data-management software package, prior to analysis. Teen relationships were found to vary along a Dis-Continuum from casual hookups to "official" boyfriend/girlfriend. There was a lack of consensus, and much ambiguity, as to the substantive meaning of different relationships. Labeling dating relationships seem to facilitate acquisition of important developmental needs such as identity, affiliation, and status, while attempting to manage cognitive dissonance and emotional disappointments. Findings underscore the confusion and complexity surrounding contemporary adolescent dating. Adolescent girls are using language and social media to assist them in meeting developmental goals. Sometimes their dating labels are adaptive, other times they are a cause of stress, or concealment of unmet needs and thwarted desires. Programs focused on positive youth development need to resonate with the realities of teens' lives and more fully acknowledge the complicated dynamics of teen dating relationships and how they are formalized, publicized and negotiated.