Begin by gathering a large mixing bowl to whisk together the all-purpose flour, unsweetened cocoa powder, baking powder, and granulated sugar. Whisk until evenly mixed, about 1-2 minutes.

In a separate bowl, pour in the milk, crack in the large eggs, and add the vanilla extract. Whisk these wet ingredients until well-combined, around 2 minutes. Slowly incorporate the wet mixture into the dry ingredients.

While your batter rests, lightly grease your waffle maker with vegetable oil or non-stick spray and preheat it.

Pour a generous amount of batter onto the center of the waffle maker. Cook for 4-5 minutes, or until the waffles are slightly crispy and puffed up.

Carefully remove the waffles and top each one with flavored whipped cream, chocolate chips for the 'buckle', and fresh fruit.