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Combine the milk, amaretto and sugar in a medium saucepan and bring to a near simmer over medium heat, stirring until the sugar dissolves.
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While the milk is heating, place the chopped chocolate in a metal bowl and set the bowl over the saucepan of milk, stirring until the chocolate is melted and smooth.
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Check every now and then to make sure the milk is not simmering.
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Whisk the melted chocolate into the hot milk mixture and keep warm.
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Whisk the whipping cream in a large bowl until soft peaks form.
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Place one scoop of ice cream in each of four bowls.
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Pour the hot chocolate mixture over the ice cream and top with the whipped cream.
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Serve immediately with spoons.