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In large microwave-safe bowl, melt Candy Melts candy according to package instructions. In small microwave-safe bowl, heat 1/3 cup cream until steaming. Add to melted candy and stir until well combined. Cool slightly.
In small bowl, whip 3/4 cup cream and confectioners' sugar to soft peaks; set aside.
Remove 1/2 cup of melted candy mixture; set aside. Put ice cream, 1/4 cup cream, and remaining candy in blender. Blend until smooth and well combined.
Pour milkshake into 4 glasses. Spoon 2 tablespoons reserved candy mixture over top of shake. Top with whipped cream and cherry.