Mentoring programs exist across the United States to provide navigation and guidance for developing youth. Mentoring as a practicecan either consist of a one-on-one mentor to mentee relationship or a group mentoring method where one mentor oversees a group of mentees. I researched ten male-to-male mentoring programs in Chicago and Washington D.C. to understand their mentoring practices and to compare them both within their own city and between the two cities. I conducted qualitative interviews with mentors and scholars on fatherhood from the Chicagoand Washington D.C.areas to understand how their mentoring practicesvary. This studydiscovered what certain programs believed to be the most effective means of mentoring, who these programs cater to, and how the youth benefit from mentors. Through my qualitative interviews, I have concluded that these male mentoring programs are not limited to but can especially benefit underserved populations. This is possibly of particular benefit toyouth growing up without resident fathers in their lives. This study concludes with a discussion of the positivesand negatives of one-on-one and group mentoring programs in Chicago and Washington D.C.This study also demonstrateshow these programs can be better used to benefitthe population that they serve. Aa a result of my findings, I recommend the implementation of fatherhood initiatives to aid the most vulnerable population targeted bymentoring programs. Additionally, I recommendthe utilization of school spaces to increase accessibility and publicity for mentoring programs. Future directions include studyingother underserved populations around the nation to understand how mentoring programs operate within those areas. Furthermore, alongitudinal cohort study could be initiated thatfollowsthe mentees’lives to further understand the positive impacts of male mentoring programs.