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Advocacy in youth mentoring refers to the advocate’s or mentor’s representation of the youth’s concerns and needs to other significant or influential people in the youth’s lives. It reflects the adults’ efforts to influence connections across different ecologies in the youth’s lives. However, an adult’s advocacy efforts may be perceived by youth as either supportive or intrusive. Indeed, we know little about how different types of advocacy contribute to the development of a strong mentoring relationship. Using data from 85 court-referred youth and their advocates (within the Youth Advocate Program) at three timepoints over four months, efforts were first made to estimate the reliability and validity evidence for two measures of youth advocacy. Second, both scales were used, along with several other interpersonal mentoring interactions at time 2, to predict the quality of the relationship at time after four months. Third, because interpersonal interactions like mentoring reflect the contributions of both individuals’ (baseline) characteristics as well as the nature of early interactions between them, dyadic analyses were used to test these associations using a structural model. These analyses reveal the way in which variation in how youth and adults interact can reciprocally influence the relationship that develops.