With a general increase in human lifespan, the need for technological advances to develop strategies for healthy aging has assumed great importance. In the present study, our goal is to predict the progression of selected aging phenotypes in a given healthy individual as they age past 65 years. Therefore, we developed a novel framework called dynamic views of aging with conditional generative adversarial networks (or DyViA-GAN) that can predict the plausible personalized trajectories of a selected aging phenotype conditioned on the available measurements of the phenotype at a few initial time instances and additional covariates. Given the prevalence of osteoporosis in the aging population, we selected the femoral neck bone mineral density (BMD) of a healthy individual as the phenotype of interest and baseline individual body mass index (BMI) as a covariate. We trained DyViA-GAN on a publicly available longitudinal dataset of a large cohort of mostly white women in the United States of age 65 years or above. It generated, for each individual, continuous phenotype trajectories, along with a corresponding region of acceptable predictions, for an age range of 66-89 years, for eight different combinations, both with and without involving the covariate. The prediction results were subjected to rigorous quality control and multiple comparative analyses. Our results clearly demonstrate the potential of generative deep learning frameworks in healthspan research.