Preheat oven to 350 degrees and line cookie sheet with parchment paper.
Beat softened butter, brown sugar, and granulated sugar with a hand or stand mixer until combined. Add eggs, vanilla extract, and milk.
1 cup Butter, 1 cup Brown Sugar, 1/2 cup Granulated Sugar, 1 1/2 teaspoon Vanilla Bean Paste, 1 Tablespoon Milk
Whisk the flour, baking soda, and salt in a separate bowl.
1 teaspoon Baking Soda, 1/2 teaspoon Salt, 2 1/2 cup Flour
Gradually add the dry ingredients to the wet mixture, mixing at low speed until combined. Be careful not to overmix.
Using a rolling pin or a meat tenderizer, break Oreos up into small pieces.
10 Oreo Cookies
Gently fold in the chocolate chips and coarsely chopped Oreo cookies until evenly distributed throughout the dough. Save a few Oreo pieces to garnish the tops of the cookies.
1 1/2 cup Chocolate Chips
Using a cookie scoop or tablespoon, drop dough balls onto the prepared baking sheet, spacing them about 2 inches apart.
Bake in the preheated oven for 10-12 minutes, or until the edges are golden brown and the centers are set. The cookies will continue to firm up as they cool.
Allow the cookies to cool on the baking sheet for 5 minutes before transferring them to a wire rack to cool completely.