How to Make It
Melt butter in a small saucepan over medium heat. Add brown sugar and pineapple and cook, stirring occasionally, until sugar has melted and pineapple is coated, about 5 minutes. Remove from heat; stir in vanilla and rum.
Place 4 waffle quarters in each of 2 serving bowls. Scoop 1/2 cup ice cream into each bowl; spoon pineapple mixture on top. Sprinkle with pecans, top with a cherry, if desired, and serve immediately.