Step 1: Prepare the Crust
- Spray the pie dish: Begin by spraying a deep pie dish with non-stick cooking spray. This will ensure that the pie comes out of the dish easily after chilling.
- Pulse the cookies: In a food processor, pulse the shortbread cookies until they reach a sand-like consistency. If you don’t have a food processor, you can place the cookies in a ziplock bag and crush them with a rolling pin.
- Mix with melted butter: In a mixing bowl, combine the cookie crumbs with the melted butter. Stir until the mixture is evenly combined.
- Press into the pie dish: Press the cookie mixture into the bottom and up the sides of the pie dish. Use the back of a spoon to press down firmly, ensuring the crust is compact and holds together.
- Chill the crust: Place the crust in the freezer while you make the filling. This will allow it to firm up quickly.
Step 2: Create the Orange Flavor
- Rinse the food processor: After using it for the crust, rinse out the food processor before making the orange filling.
- Puree the orange mixture: Add the peeled and sliced orange, orange zest, vanilla extract, and orange juice to the food processor. Puree the mixture until it’s smooth and well-combined. Set it aside.
Step 3: Make the Filling Base
- Combine cream cheese and Jello mix: In a stand mixer (or large mixing bowl with a hand mixer), combine 8 ounces of cream cheese and the orange Jello mix. Beat until smooth and well-incorporated.
- Add sweetened condensed milk: Fold in the sweetened condensed milk to the mixture. This will create a creamy, rich base for the filling.
- Combine until smooth: Continue mixing until the filling is smooth and velvety.
Step 4: Make the Filling Fluffy
- Add Cool Whip: Fold in 8 ounces of Cool Whip, which will make the filling airy and light. Gently incorporate the Cool Whip to maintain the fluffiness of the mixture.
- Whip it to perfection: If you prefer an even fluffier filling, you can whip the Cool Whip and cream cheese mixture before folding them into the Jello base.
Step 5: Assemble the Pie
- Pour the filling into the crust: Carefully pour the filling into the pie crust, spreading it evenly with a rubber spatula. Smooth the top of the pie to ensure it’s level.
- Chill the pie: Place the pie in the fridge for a couple of hours for a soft-serve texture. For a firmer, frozen dessert, place it in the freezer for an hour.
Step 6: Make the Topping
- Whip the cream cheese and Cool Whip: In a separate bowl, whip the remaining cream cheese and Cool Whip until smooth and fluffy.
- Spread the topping: Once the pie has chilled, spread the whipped cream mixture over the top of the pie, covering it completely.
Step 7: Garnish and Serve
- Garnish with orange slices: Top the pie with fresh orange slices to add a burst of color and flavor.
- Serve and enjoy: Slice the pie and serve it to your friends and family. Enjoy the cool, creamy goodness of this delightful dessert!