Fill 4 6-ounce heatproof glasses or clear mugs with hot water.
In a medium saucepan, melt chocolate in milk. Whisk until it comes to a boil, then continue whisking for 1 minute.
Empty the glasses and pour 1/4 cup of hot chocolate into each. Over the back of a spoon, gently pour 1/4 cup of coffee on top of hot chocolate. Top off each glass with 1/4 c whipped cream and serve.