Preheat oven to 350°F. Remove the cookie dough from the fridge, and let it sit on the counter for 15-20 minutes to allow it to soften. .
Spread macadamia nuts on a cookie sheet in a single layer. Toast for 6-8 minutes until lightly golden. Cool completely before incorporating into the cookie dough.
To assemble cookie bowls: In a medium size bowl, mix cookie dough, 1/2 cup toasted macadamia nuts, and toffee bits together until evenly distributed.
Spray the muffin cups liberally with cooking spray. Divide cookie dough evenly pressing onto the bottom and 2/3 up sides of each cup.
Bake for 14-16 minutes or until a toothpick inserted into the center comes out clean. Set the cookie bowls aside to cool for several minutes before attempting to remove them from the pan. Run a knife around the edge and gently lift to remove to a cooling rack.
To make pineapple kabobs: In a small bowl, mix together melted butter, brown sugar and cinnamon. Thread the pineapple chunks onto the bamboo skewers, and brush lightly with the butter glaze.
Grill the kabobs over medium-high heat until the sugar has caramelized turning carefully so to brown all sides. Continue to baste with butter each time you turn the kabobs for around 5-7 minutes total. (Watch closely since the sugar will caramelize quickly and can burn very easily.)
To serve: Warm the caramel sauce in the microwave. Place the cookie bowl onto a serving plate and top with a scoop, or two, of vanilla ice cream.
Arrange the pineapple kabobs around the bowl and drizzle everything with warm caramel sauce.
Garnish with toasted macadamia nuts and serve immediately.