Add pitted and chopped dates to a blender or food processor with milk, and vanilla extract. Blend for about 1 minute, until the mixture is as smooth as possible.
In a small pot, over medium-high heat, add the blended mixture, and let it bubble and simmer for about 2 minutes, stirring frequently until the mixture is a bit frothy.
In a small mixing bowl stir together yogurt and vanilla bean paste until combined.
Layer 1/3 of the yogurt into the bottom of each serving glass.
Alternate layers of granola, date sauce, pumpkin seeds, cranberries, sliced banana, and pumpkin pie spice with the yogurt, until the glasses have been filled to the top.
Serve parfaits immediately to ensure the granola stays crunchy.