Preheat the oven to 350°F. Grease a standard 12 count muffin tin with baking spray and set aside. Optional: you can dust a sprinkle of flour in each well too, to help cookie cups release from pan.
Place the butter and sugars in the bowl of a stand mixer. Secure the paddle attachment and cream until light and fluffy, ~3 minutes.
3/4 cup unsalted butter, softened, 3/4 cup brown sugar (dark or light), packed, 1/2 cup granulated sugar
Then, add in the egg and vanilla extract. Blend until mixed. If any of the mixture gets stuck on the paddle attachment or side of the bowl, use a rubber spatula to knock it off.
1 large egg, room temperature, 1 tsp. vanilla extract
Add in the dry ingredients and mix together on low speed.
2 1/4 cup all-purpose flour, spooned and leveled, 1, 3.4 oz. box instant vanilla pudding mix*, 1 tsp. baking soda, 1 tsp. baking powder, 3/4 tsp. salt
Add in the mini chocolate chips and incorporate just until combined.
1/2 cup mini semi sweet chocolate chips
Scoop the cookie dough into prepared muffin tin, ~3 tbsp in each. No need to roll into a ball or press cookie dough down, the cookies take shape in the well of the muffin tins as they bake. Bake for ~15-17 minutes, or until edges begin turning light golden brown. The center will be a little underdone.
Once removed from the oven, they will have a slight indentation in the middle. Take a spoon, and gently press the cookie down and toward the edges to create a cup shape. Once again, they cookie may seem a little underdone, but it’s OK. They’re just gooey and warm!
Allow to cool in the muffin pan for ~15-30 minutes before removing from pan; this makes it easier and ensures they won’t break. Run a knife around the edges to release them onto a wire cooling rack.
Once completely cooled, scoop ice cream into the cups, garnish with your favorite ice cream toppings and enjoy! OR you can warm the cookie cup in the microwave for a few seconds then add a scoop of ice cream for a warm cookie pizookie vibe!
for serving: vanilla ice cream, caramel sauce, sprinkles, chocolate fudge, etc.