This qualitative study explores the youth-initiated mentoring (YIM) approach for youth at risk for out-of-home placement. In this approach, a youth nominates someone from within their social network, and positions this person as a YIM to function as an ally for the youth and as a partner for parents and professional caregivers. Through interviews with six youth, six YIMs, and seven parents (N = 19), we examined the positioning of a YIM and sustainability. The results indicated that attitudes from participants toward asking someone or being asked to become a YIM varied from enthusiastic to cautious. Participants reported increased contact intensity and relationship quality. Two parents did not experience YIM as beneficial. Most participants expected that the YIM-mentee relationship lasts after professional care terminates. The results reveal that YIM is experienced as an ally, but it also has the potential to increase relational conflicts between social network members.