Leave cream cheese out of the refrigerator for half an hour or until softened. Remove the center and tops of the strawberries.
Use an electric beater to mix the confectioners’ sugar, vanilla extract and cream cheese until they are smooth. Spoon the mixture into a bag (piping bag or plastic bag with corner cut off).
Squeeze the mixture into each strawberry. Gently melt the chocolate in the microwave, stir, and drizzle over the strawberries.