This phenomenological study of cross-cultural mentoring is set in an online health workforce development program for youth from backgrounds underrepresented in medicine (URIM). The purpose of this study is to understand how personal and contextual factors influence the experiences of medical student mentors. This study provides insights into how mentoring programs can support the development of positive cross-cultural relationships in online environments. A literature review identified individual and contextual influences that contribute to mentoring relationship quality. How these factors translate through online modalities is underexplored in the literature on youth mentoring. This research used mixed methods in a case-selection variation of an explanatory sequential design, prioritizing the qualitative strand. In the study's first phase, medical student mentors completed a written questionnaire to reflect on their experiences mentoring youth in virtual settings. Participants were selected for the study's second phase using a stratified purposeful sample to represent the demographics and the variation in responses among phase one respondents. Phase two data collection involved open-ended, semi-structured interviews designed to more deeply re-explore the textual and structural themes that emerged from mentors' written reflections. This research informs the development of online mentoring programs by considering the influences of program structure and design, mentor and mentee preparation, online tools, and cross-cultural training on the quality of mentorships. It addresses a gap in the literature by exploring the experience of mentoring relationships in online settings. The research questions guiding this study are: 1. How do medical students experience their cross-cultural mentorships with URIM youth in online health career exploration programs? 2. How do mentors describe the role of the online context of mentorship in their experiences? [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.]