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Step 1
Using a standing mixer fitted with the whisk attachment or an electric mixer, whip the heavy cream until stiff peaks form.
Step 2
Meanwhile, in a medium bowl, combine ricotta, powdered sugar, and 2 teaspoons vanilla. Fold in whipped cream, cover, and refrigerate while making the Pizzelle cookies.
Step 3
Preheat Pizzelle iron and lightly coat with nonstick cooking spray.
Step 4
In a large bowl, combine flour, sugar, butter, eggs, vanilla, and baking powder. Drop slightly rounded tablespoons of batter on to Pizzelle iron and close. Bake as directed by manufacturer or until golden brown, 30 seconds to 1 minute.
Step 5
Using a nonstick spatula, remove one pizzelle, leaving the second still on the open press, carefully wrap around a ¾” wooden dowel and pinch where the ends of the cookie meet. Hold until pizzelle is cool enough to retain its shape, using a kitchen towel if necessary to prevent burning your fingers. Repeat with second cookie on press and all remaining batter.
Step 6
Remove filling from the refrigerator and fold in chocolate chips. Using a pastry bag fitted with only a large coupler and no tip, pipe the filling into each side of a cooled pizzelle. It is okay if the filling does not go all the way through the middle of the cookie.
Step 7
Garnish with additional chocolate chips and dust with powdered sugar if desired. Serve immediately or chill until serving time.