Preheat the oven to 400°F.

Place the bananas, still in their peels, on a rimmed baking sheet. Roast the bananas for 15-20 minutes, or until the peels have turned black and they look shiny and swollen. Remove the pan from the oven and let cool to at least room temperature before handling them.

Cut the tip off of the banana peels and squeeze the room temperature, soft, roasted bananas into the blender. Add the ice cream and 1/4 cup of milk. Blend until smooth. If a thicker milkshake is desired, you can blend in several ice cubes to thicken it. If you'd like it thinner, add the remaining 1/4 cup of milk.

Take 2 pint jars, or similarly sized glasses, and drizzle some of the caramel sauce around the inside rim. Let it drip down before dividing the milkshake between the two cups. Top each glass with a generous cap of whipped cream then drizzle a little more caramel sauce and some chocolate sauce on top. Nestle a bruleed banana half in the whipped cream and serve immediately! Leftovers can be poured into popsicle molds for wonderful banana cream popsicles.