Preheat oven to 350 degrees and grease a 9 inch heat-proof skillet.
In a large mixing bowl, whisk together all-purpose flour, baking powder, baking soda, salt, and brown sugar until combined.
Make a well in the center of the dry ingredients and add in the olive oil and milk into the center. Whisk together the milk and olive oil until combined (it's okay if a little of the dry ingredients gets in there) and then switch to a wooden spoon to mix everything together until just combined.
Add 3/4 of the chocolate chips and mix until incorporated. Transfer to greased pan and press down dough evenly down onto pan. Sprinkle remaining 1/4 cup chocolate chips on the top.
Bake for 30 minutes or until golden brown. Remove from oven and let cool slightly.
When ready to serve, scoop Hudsonville Dairy-Free Caramel Cookie Dough Ice Cream over the top, add sprinkles, chocolate chips or chocolate syrup, and top with cherries. Pass around spoons and dig in!