In the area of positive youth development, mentoring programs are often looked upon to help disadvantaged youth connect with caring adults in order to increase positive behaviors and decrease negative behaviors. The benefits of these programs were often assumed and it was not until recently that large-scale research has examined their effectiveness. The results of the research are modest, at best, suggesting that youth mentoring programs provide only minimal benefits to its participants. A closer examination of the research reveals that the effectiveness of the programs increased if they adhered to specific practices, in particular specific aspects of the mentoring relationship. The aspects of the mentoring relationship that contributed to greater effects include emotional expressiveness by the youth and non-hierarchical collaboration between the youth and mentor. Although theories on mentoring have not been well-established, many point to the life-span development literature as the basis for their effectiveness. However, these theories may be based on a Western worldview of mentoring relationships that contradict with Eastern values of emotional moderation and hierarchical relationships. Current mentoring programs may be less salient to Asian populations, specifically the notion that successful mentoring requires emotional expressiveness and non-hierarchical relationships. This study examined the acculturation level of Asian participants and its impact on distress disclosure, willingness to emotionally-self-disclose to peers and mentors during early adolescence, and relational health with peers and mentors during early adolescence. Values acculturation significantly predicted distress disclosure but did not predict emotional self-disclosure. However, the number of years lived in the U.S. did predict emotional self-disclosure. No interactions were found for relational health and emotional self-disclosure across values acculturation level and relationship type; main effects were found for both variables in that relational health and emotional self-disclosure tended to be less with mentors than with peers. Exploratory analyses using behavioral acculturation found an interaction for emotional self-disclosure across relationship type; those who were less acculturated were more willing to disclose emotions to mentors during early adolescence, a finding in an unanticipated direction. The behavioral and values aspect of acculturation is discussed as well as the cultural influence of the community in mentoring.