Purpose/objectives: Dental students face many challenges throughout their education. Peer mentoring programs can support students and help manage pressures associated with dental school, although few studies have researched student-led peer mentoring. The aim of this study was to explore the possibilities and limits of student-led, near-peer mentoring in a dental program. Methods: We conducted a qualitative study on the tooth bud program (TBP), a student-led, near-peer mentoring program at a research-intensive university. Eligible study participants were Doctor of Dental Medicine (DMD) students who participated in the TBP as a first-year mentee and/or second-year mentor between 2017 and 2020. Twenty-two participants and one program founder were interviewed about their experiences and involvement in peer mentoring. A thematic analysis was employed, and Brownlie and Anderson's sociology of kindness provided a theoretical analytical framework.Results: Three themes represented participant perspectives of the TBP: Firstly, students desired to build a community but had to manage inherent hierarchies.Secondly, participants appreciated that the TBP was a student-led initiative, but its unstructured and informal nature brought challenges. Thirdly, mentoring experiences and the ways mentors and mentees navigated their pairings were identified. Conclusions: Mentoring was founded in the shared experience of studying dentistry and allowed mentor-mentee pairs to establish kinship and progress relationships. Kindness acts as an infrastructure to guide interactions; however, underdeveloped kinship may hinder mentoring. Thus, the peer mentoring program researched provides value to mentees and mentors and allows participants to benefit from becoming part of a student-led, professional community.