Dip the rim of two glasses in water, then into the crushed caramel candy. Set aside.
Puree milk and dates in a blender until well combined (until there are virtually no date bits and pieces). Add frozen pineapple chunks, almond butter, vanilla and maple extracts, salt, and ice cubes. Blend on medium speed until ice cubes are pureed and beverage is thick and frothy.
Divide between the 2 candy rimmed glasses and add a pinch of sea salt on each, if desired.