Young people from foster care face numerous challenges and barriers in their transition to adulthood and engagement with higher education. Foster alumni are one of the most disadvantaged student populations, compelling educators and policy makers to create pathways leading to student success. This qualitative life history explores the journey of one foster alumnus from high school drop out to four-year college scholarship recipient. Narrative intimate inquiry frames this study. A critical lens is used to view the identity capital of one raised by surrogate parents—the state. Jean serves as the heart of this study; I serve as a co-constructor in bringing her story to life. I explore how the life of one speaks to the plight of many and how we can smooth out the transition processes for this underserved, historically marginalized group of young people seeking stability. In addition, this study explores intimateness in inquiry. Intimate inquiry bringing to the forefront a critical conversation of how love and relationship with participants adds dimension to both scholarly contribution of findings and the rich nuances of researcher-participant engagement.