Pit them. If they're dry, soak in hot water for 5–10 minutes, then drain well. Soft dates blend smoother and sweeter.
Add dates, milk, vanilla, cinnamon, and salt to the blender. Blend on high until the dates are fully pulverized and the mixture looks silky.
Add ice and blend again until thick and frosty. Start with 1 cup and add more to reach that milkshake-level thickness.
Need sweeter? Add half a date. Too thick? Splash in more milk. Too thin? More ice or a spoonful of yogurt.
Blend in a tablespoon of almond butter or a pinch of cardamom for depth, or a shot of espresso for caffeine magic.
Pour into a chilled glass, dust with a little cinnamon on top, and flex on your taste buds.