Wash raspberries very gently in cool water and carefully dry with paper towels. Let stand at room temperature for about 30 minutes to ensure the raspberries are completely dry. Don’t dip raspberries unless they are completely dry otherwise chocolate will become cloudy or won’t stick to the berries.
Line a large sheet pan with parchment paper, wax paper, or a silicone baking mat and set it aside. If using baking bars, coarsely chop the chocolate. Be patient when melting the chocolate and avoid rapid temperature changes. Do not microwave for too long or too many times; stir the chocolate frequently as it melts. Allow the coated raspberries to harden at room temperature instead of refrigerating or freezing them.
Add all but 2 tablespoons of the chocolate melting wafers to a large microwave-safe bowl (see note 3). Add 1 teaspoon oil. Microwave for 15 seconds, then stir vigorously for 15 seconds. Continue to do this until the chocolate is melted. Once melted, add the reserved 2 tablespoons of chocolate and stir until it melts (see note 4). Be patient and resist the urge to microwave unless it isn’t melting after stirring for a full minute.
Once the chocolate is fully melted and smooth, gently dip the bottom 2/3rds of the raspberries into the melted chocolate Carefully slide the bottom of the raspberry against the edge of the bowl to remove any excess chocolate. Place the raspberry on the lined sheet pan. Repeat with remaining raspberries. If the melted chocolate is getting too hard to dip, heat it in the microwave for another 15 seconds and remix. You may need to add 1/2 teaspoon of oil too.
If you would like to fill your raspberries, use a hand mixer to beat softened cream cheese, granulated sugar, and vanilla extract in a medium bowl until completely smooth. Use a spatula to scrape every bit of this mixture into a plastic bag. Using scissors, cut off enough of the tip to pipe the mixture into raspberries. Pipe the cheesecake filling evenly among all the raspberries. Leave chocolate at room temperature to harden completely.
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Notes
Note 1: Chocolate chips have stabilizers that prevent smooth melting. For better results, use high-quality baking bars like Baker's, Lindt, or Ghirardelli, or try melting wafers. Choose any chocolate you prefer—milk, semi-sweet, dark, or white.Note 2: Choose the freshest raspberries available! Look for bright red, firm, and plump berries without any soft spots. I recommend buying a larger container, so you have plenty to choose from in case some aren't in perfect condition.Note 3: To prevent scorching the chocolate, melt it in very short bursts and stir frequently. The goal is to keep the chocolate warm enough to melt gradually, but not hot; it should reach a smooth, room temperature consistency.Note 4: Slowly melting chocolate and stirring often prevents streaks by stopping the cocoa butter from rising. Adding unmelted chocolate at the end helps it set with a smooth, glossy finish that won't melt easily on your fingers.Nutrition Note: Calories do not include the optional cheesecake filling. With the cheesecake filling, each raspberry is about 34 calories.Storage: Chocolate Covered Raspberries are best enjoyed the same day. They last 8–10 hours in a cool, dry place before becoming sticky. Avoid refrigerating, as condensation can cause the chocolate to crack.