In a medium bowl, combine the sliced strawberries, heavy whipping cream, powdered sugar, and vanilla extract.
Using an electric mixer, whip the mixture on medium-high speed until soft peaks form, about 3-5 minutes.
Prepare the skewers by alternating threading the angel food cake cubes and whole strawberries until filled.
Transfer the whipped dip to a serving bowl.
If desired, melt the chocolate chips in a microwave-safe bowl in 30-second intervals, stirring in between until smooth, and drizzle over the whipped dip.
Serve the whipped strawberry dip alongside the shortcake skewers for dipping.