01 - Prepare vanilla cake according to package directions or your preferred recipe. Allow cake to cool completely before proceeding with crumbling.
02 - Beat softened cream cheese and butter in a medium bowl until smooth. Gradually incorporate powdered sugar and vanilla extract, mixing until creamy and well-combined.
03 - Crumble cooled cake into fine pieces in a large bowl. Add frosting one spoonful at a time, mixing until the mixture holds together when pressed but remains pliable enough for shaping.
04 - Portion mixture into 24 equal pieces. Roll each into a ball, then gently flatten and shape into a teardrop or triangle form to resemble watermelon slice cross-sections.
05 - Melt a small portion of green candy melts. Dip the tip of each lollipop stick into the melted coating, then insert approximately 1 inch into each shaped cake pop. Place in freezer for 20 minutes to set.
06 - Melt pink or red candy melts with 1 teaspoon vegetable oil if needed to achieve smooth consistency. Dip each chilled cake pop into the pink coating, allowing excess to drip off. Immediately press mini chocolate chips into the wet surface as watermelon seeds.
07 - Melt green candy melts separately. Dip the bottom portion of each coated cake pop into the green coating to create the watermelon rind effect. Stand pops upright in a cake pop stand or styrofoam block until completely set.
08 - Refrigerate until firm, at least 30 minutes. Serve chilled or at room temperature. Store in an airtight container in the refrigerator for up to 3 days.