Most of the existing body of research on formal youth mentoring has focused on programs in the United States, with few inquiries into how mentoring programs have taken shape in other contexts. In this article, we compare and contrast programs in the United States and continental Europe to investigate how context shapes the ways in which programs are conceived and implemented. Concerns about inequality and delinquency have been major drivers of program expansion in the United States, while concerns about the influx of migrants into linguistically and culturally homogeneous communities have fostered the expansion of programs in continental Europe. Through a series of program comparisons, we explored differences in volunteer characteristics, target populations, and how programs and benefits are construed. Implications for implementation and future research across both contexts are discussed.