This study examines long-distance relationships between grandparents and their adolescent grandchild through the qualitative identification and analysis of relational turning points and trajectories. A sample of 30 grandparents yielding 99 individual turning points allowed for an in-depth understanding of these relational constructs that previous research neglects to explore from the perspective of a grandparent. A constant comparative analysis of these turning points reveals 8 distinct categories of relational turning points including Spending Time Together, Family Relational Dynamics, Geographic Distance, Lack of Relational Investment, Use of Technology, Relational Investment, Lack of Free Time, and Grandchild Gaining Independence. These turning points vary in how they positively or negatively impact relational closeness between participants and their grandchildren. The use of Retrospective Interview Technique (RIT) yields 30 individual relational trajectory graphs categorized into five trajectories including Decrease in Closeness, Increase in Closeness, Multidimensional Changes in Closeness, Minimal Changes in Closeness, and Consistent Relational Closeness. Results provide theoretical contributions to aging and family literature as well as practical findings pertaining to current and future grandparents. These implications as well as suggestions for future research are discussed.