Mentoring has long been a strategy leveraged to support college students' development and academic success. The majority of studies on mentoring have focused on formal mentoring programs that involve a structure and the support of a program administrator. Studies have focused on mentorship outcomes such as increased academic achievement, persistence and retention, and career support. However, research focused on informal mentoring and the process of initiating and developing a relationship remains limited. This study uses qualitative interview data from 6 faculty and undergraduate student mentoring dyads to understand how participants initiate and further develop informal mentoring relationships and the perceived benefits from the vantage point of both dyad members. The study took place at an urban, Midwestern university. The findings of this study offer insights into how faculty and students provide cues to one another during the initiation stage and help establish shared expectations during the cultivation stage of their relationship. Additionally, the study identifies an opportunity to design professional development workshops to assist faculty in establishing a mentoring philosophy to make this meaningful work more manageable. [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.]