01 - Prepare vanilla cake according to package directions or your preferred recipe. Bake until fully cooked, then allow to cool completely at room temperature.
02 - Beat softened cream cheese and butter together until creamy. Gradually incorporate powdered sugar and vanilla extract, mixing until smooth and spreadable.
03 - Crumble cooled cake into fine pieces in a large mixing bowl. Add frosting gradually, mixing by hand until combined. The mixture should hold its shape when pressed but remain moist and pliable.
04 - Portion mixture into 24 equal pieces. Roll each into a ball, then gently press into a teardrop or triangular wedge shape resembling a watermelon slice.
05 - Melt a small portion of green candy melts. Dip the tip of each lollipop stick into melted candy, then insert approximately 1 inch into the center of each shaped cake pop. Place in freezer for 20 minutes to set firmly.
06 - Melt pink or red candy melts with 1 teaspoon vegetable oil if needed for smooth consistency. Working quickly, dip each chilled cake pop into the pink melts, covering all but the very bottom. Allow excess coating to drip off, then immediately press mini chocolate chips onto the wet surface as watermelon seeds.
07 - Melt green candy melts. Dip the exposed bottom portion of each cake pop into green melts to form the watermelon rind. Insert sticks into a cake pop stand or foam block to set upright. Allow coating to harden completely at room temperature or refrigerate for faster setting.