This article will summarize research on youth mentoring and aims to answer the following questions: (1) Does it matter whether mentors and mentees are matched on race and ethnicity? (2) Are same-race matches necessarily more beneficial than cross-race matches? (3) Do ethnicity and race affect the way mentors and mentees relate? (4) Are there other ways in which mentors, and mentoring programs, can foster cultural sensitivity in mentoring relationships?