The purpose was to develop and document—in an on-site, participatory framework for change—youth workers’ confrontational difficulties in the caretaking of marginalized teens. Although the dynamics of confrontations are well documented and training programs are in place, little attention has been paid to the lived-experiences of these teacher-counselors. In remedy, inquiry explored this little-studied arena in a small segment of residential care of the estimated 1.5 million homeless adolescents in the United States.

Qualitative research questions (e.g., what’s going on here?) yielded first-person recollections (compared with literature on confrontational anger). Data from semistructured, phenomenological interviews were thus descriptive and reflective. Researcher analyses were thematic and member-checked, with consensual understanding as the goal. The data source was entry-level teacher-counselors, self-selected volunteers from a population of 40 from 4 residential shelters. The number of participants was 6, enough to reach diminishing insight in analysis, yet reflect the demographics of the participant pool.

Hermeneutic phenomenology was chosen for in-depth access to participants’ implicit and experiential knowledge. Using guiding psychodynamic constructs, transference and countertransference, the method consisted of researcher analysis of a transcribed series of 3 interviews per participant. The first elicited descriptions of individual confrontations and reflections on them. The second provided reviews of the first and reflections on the possibility of transference. The third focused on countertransference with reviews of themes.

Research findings present transferences, recognized as relational, and the ways in which confrontations seriously affect the quality of caretaking. Examples of countertransference, however, proved difficult to explore directly. Negative consequences attributed to long-term exposure to confrontations are neither confirmed nor disconfirmed.

Limitations to method and sample size are discussed, as are possible modifications and implications for future studies. Addressing the organization, trainers, and coworkers, recommendations highlighted arenas for change—primarily, in cooperative teamwork and communicative openness. The research may contribute: (1) insight into teacher-counselors’ lived experiences; (2) practical knowledge to develop training strategies and sustainable efforts toward teacher-counselor self care; and as a derivative result, (3) improvement in residential services for troubled youth.