Crush the Cookies
Place Golden Oreos in a food processor and pulse until fine crumbs form (like sand).
Alternatively, crush in a zip-top bag using a rolling pin.
Set aside ½ cup for topping.
Prepare Pudding
In a bowl, whisk instant pudding mix with cold milk for 2 minutes.
Let sit 5 minutes to thicken.
Make Cream Cheese Mixture
Beat softened cream cheese until smooth.
Add powdered sugar and mix until combined.
Stir in vanilla extract if using.
Gently fold in whipped topping.
Combine
Fold prepared pudding into the cream cheese mixture until smooth and fluffy.
Assemble Cups
Add a layer of crushed cookies to the bottom of clear cups.
Spoon pudding mixture on top.
Add another layer of cookie crumbs.
Repeat layers until cups are filled.
Finish with cookie crumbs on top.
Chill
Refrigerate for at least 1–2 hours before serving.
Decorate & Serve
Add gummy worms, candy seashells, or umbrellas just before serving.