Preheat waffle iron according to manufacturers directions. I used the highest heat setting on my waffle iron, and let the waffles cook one minute longer than the beep. I also sprayed my waffle iron with nonstick cooking spray.
To start on the batter, melt butter and chocolate chips together in a small microwave safe bowl, stirring at 20 second intervals, until smooth. Set aside to cool slightly.
In a medium bowl, whisk together flour, sugar, baking powder, salt, and cocoa powder.
To the dry ingredients, add milk, eggs, and vanilla. Whisk together to combine.
Stir in the melted butter and chocolate, and mix until well incorporated.
Cook waffles according to manufacturer’s directions. I used a full 1/2 cup scoop of batter for each waffle.
Remove waffles to a plate, and top with additional chocolate chips, powdered sugar, whipped cream, and fresh raspberries.
The waffles will feel soft when first removed, but the outside will crisp up as it cools.