In a large mixing bowl, beat together 1 cup softened unsalted butter, 1 cup brown sugar, 1 cup granulated sugar, and 1 teaspoon vanilla extract until light and creamy.
Mix in 2 tablespoons milk until combined.
Stir in 2 cups all-purpose flour and ½ teaspoon salt by hand until a dough forms. Add a little more milk if needed until the dough comes together.
Fold in 1 cup semi-sweet chocolate chips.
Roll the cookie dough into approximately 20 balls and refrigerate until you are ready to fry them.
Heat 3 inches of oil in a deep pot.
In a medium bowl, whisk together 1½ cups pancake mix, 1 large egg, 1 cup milk, 2 teaspoons vegetable oil, and 1 teaspoon vanilla extract until smooth.
Dip each cookie dough into the batter, then place in the oil.
Cook for 3-4 minutes, turning occasionally until golden brown.
Place the fried cookie dough on a serving plate and top with the powdered sugar. Enjoy!