This qualitative research aimed to identify factors contributing to the formation and development of effective partnerships that foster positive youth development. The study involved interviews with eight adult military mentors and nine youth cadet mentees to gain various perspectives regarding mentoring relationships within the youth leadership program at Oakland Military Institute (OMI). The responses were analyzed with "in vivo" coding, sorted into patterns, and condensed into four themes for the adult respondents and three themes for the youth respondents. The themes revealed that successful relationship initiation and cultivation depends on specific identifiable mentor characteristics, behaviors, and actions, which lead to closer bonds than routine interactions and often lead to mentees developing into mentors themselves. Possessing relevant experience, such as overcoming adverse childhood experiences, was the most important factor for converting initial contacts into deeper connections. Successful mentoring relationships take on a familial character and are often described as "parental" or "fatherly." Youth may affiliate with several mentors, some of whom provide general mentoring and others who offer functional mentoring for a specific skill or life event the youth is learning about, such as computer programming or college admissions. Mentoring is an essential tool that can assist youth in successfully transitioning to young adulthood; it is precious for disadvantaged youth with a cultural or social capital deficit. The most important factor for initiating and cultivating a relationship is that the adult, who holds the benefits of accrued knowledge, experience, and skill, must try to connect with the younger person. Recommendations derived from this research include that OMI institutionalize mentoring as a specified role for the military staff; that OMI develop a formal mentoring policy, procedures, and goals; the mentoring program include criteria to identify cadets who would most benefit from focused outreach and deliberate mentoring opportunities; and the mentoring program also intentionally create situations where cadets and adults work together in small groups to foster relationship formation. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]