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Place the pineapple spears on a wax paper lined baking sheet.
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Insert one lollipop or popsicle stick vertically into each pineapple spear. Place baking sheet into the refrigerator while you melt the chocolate.
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Place 1 ½ bags of dark chocolate melting wafers into a tall microwave safe container. Heat in the microwave, stirring every 30 seconds until melted.
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Remove the pineapple spears from the refrigerator and dip each one into the chocolate, fully covering all sides.
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Place dipped pineapple spears back onto the wax paper lined baking sheet and return to the refrigerator to set, about 15 minutes.
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Meanwhile, place the remaining dark chocolate melting wafers into the tall microwave safe container. Heat in the microwave, stirring every 30 seconds, until melted.
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Remove the pineapple spears from the refrigerator and dip them into the chocolate to create a second layer of dark chocolate.
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Place the freshly dipped pineapple spears back on the wax paper and return to the refrigerator to set, about 15 minutes.
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Place the white chocolate melting wafers into a piping bag. Heat in the microwave, massaging the bag every 30 seconds, until melted.
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Remove the pineapple spears from the refrigerator and pipe a drizzle of white chocolate onto each spear.
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Let the chocolate set and enjoy. Store any remaining pineapple in the refrigerator.