Preheat and grease a waffle iron according to manufacturer's instructions.
Whisk flour, sugar, baking powder, and salt together in a large bowl.
Whisk milk, eggs, butter, and vanilla extract together in a separate bowl; stir into flour mixture just until batter is moistened.
Pour 2 teaspoons batter into the preheated waffle iron for each waffle, leaving spaces between each. Insert a lollipop stick about 3/4 of the way into each pool of batter; close the lid. Cook until golden and crispy, about 1 minute. Transfer each waffle pop to a cooling rack and repeat with the remaining batter.
Melt dark chocolate chips in a microwave-safe glass or ceramic bowl in 15-second intervals, stirring after each melting, 1 to 3 minutes. Transfer melted dark chocolate to a pastry bag fitted with a small writing tip or a resealable plastic bag with the corner snipped; drizzle over 1 side of each waffle pop.
Melt white chocolate chips in a microwave-safe glass or ceramic bowl in 15-second intervals, stirring after each interval, 1 to 3 minutes. Transfer melted white chocolate to a pastry bag fitted with a small writing tip or a resealable plastic bag with the corner snipped; drizzle over the dark chocolate.
Sprinkle coconut and macadamia nuts over the melted chocolate, pressing lightly to help toppings stick while chocolate cools and firms.
