01 - Place milk, softened cream cheese, vanilla ice cream, strawberries, granulated sugar, and vanilla extract into a blender container.
02 - Blend on high speed until completely smooth and creamy, stopping to scrape down the sides of the blender as needed to ensure even incorporation.
03 - Taste the milkshake and add additional sugar if desired, blending briefly to incorporate any adjustments.
04 - Pour the finished milkshake into two chilled glasses. Top with whipped cream, crushed graham crackers, and fresh strawberry slices if desired. Serve immediately with straws.