Make them virgin for the kids, then indulge yourself. This is what the 'bad kids' had in the fifties, hiding flasks under their poodle skirts and sneaking them into cherry milkshakes at the local diner. Common, you know you want to ; )
Step 1 - Preheat oven to 350*F and line a small baking pan with parchment paper. Spread out pitted cherries and drizzle one tbsp olive oil and balsamic, tossing cherries to coat. Roast in the oven for 20 minutes, then remove and cool to room temperature.
Step 2 - In a bowl, beat whipping cream until thickened - about 3-4 minutes. Beat in icing sugar and bourbon until just combined, maybe 1 minute and set aside.
Step 3 - In a blender add ice cream, rum, milk, remaining 1 tbsp olive oil, and roasted cherries and blend until smooth! If it's too thin for your liking, add extra ice cream. More milk if too thick! Fill glasses with milkshake, a drizzle of Cherry Balsamic, then whipped cream. Top with the most perfect (pitted) cherry and a straw!