Open the Brownie Bites, (1 individual Package) and crumble the Brownies into small pieces.
Place the Melting Chocolate on a plate or shallow dish, and melt it in the microwave.
Dip the Rim of the Glass in the melted Chocolate, and immediately in the crumbled Brownie pieces.
Place the Glass in the Freezer to set the Chocolate.
In a large Pitcher, add the Milk, Bailey's, and Ice Cream, and stir until thick and creamy.
Remove the Glass from the freezer, and pour the Milkshake into the Glass.
Add a generous amount of whipped cream, and top with a Cherry.
Sprinkle Crumbled Brownies on top of the Whipped Cream.
Add a festive straw, or two, Serve, and Enjoy!!!!