Drain the cottage cheese, if needed. (The less liquid you start with, the thicker the pudding).
Combine the cottage cheese, maple syrup, vanilla, and half the banana slices in a mini food processor or high-speed personal blender. Process until smooth, scraping down the bottom and sides as needed. Taste and add more maple syrup until it's your preferred level of sweetness.
Add one-third of the pudding mixture to the now-empty cottage cheese cup (or small bowl). Crumble in a cookie or two (exactly how many you need will depend on what size your cookies are. I use two cinnamon thins per layer). Add half of the remaining banana slices.
Add another one-third of the pudding mixture, followed by more cookies and the remaining banana slices. Top with the remaining pudding. Enjoy immediately, or refrigerate up to overnight (the longer it sits, the softer the cookies will become, so this is just personal preference). Top with a few more cookie crumbles before serving.