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As college degrees become increasingly standard expectations for middle-to-high wage positions in the workforce, growing numbers of children and parents in the United States are accruing and repaying loans for postsecondary education. At the same time, the United States is witnessing unprecedented rates of longevity and a subsequent need for more intentional financial planning for retirement that starts earlier in life. The goal of this three-paper dissertation is to explore how student loans are experienced within families and discover the ways in which borrowers of different ages perceive and prioritize retirement and longevity-planning in light of their student loans. Utilizing qualitative and quantitative data collected through a concurrent triangulation mixed methods study design, the first two papers explored how student loan borrowers make, negotiate, and experience student loans within their family of origin. Paper 1 focused on the family context of borrowers repaying loans for their own education, and Paper 2 focused on the family context of borrowers repaying loans for a child or grandchildren education, several of whom were also repaying additional loans for their own educational expenses. Ultimately, the ways in which families communicated about student loans during repayment played at least a partial role in how they experienced the loans as part of their overall family dynamics. Shifting from a focus on family dynamics to longevity planning, Paper 3 focused on ways in which borrowers perceive and plan for longevity in light of the loans they carry for themselves and/or family members. Results suggest that planning for future financial security for oneself and/or family members may be less achievable with the presence of student loan debt. The main contribution of this dissertation is its attempt to understand the ways in which borrowers experience student loans in family systems and longevity planning contexts. This dissertation has also highlighted gaps in knowledge that policymakers, practitioners, and scholars can begin to address with current and potential student loan borrowers.