01 - Place the cream cheese, whole milk, vanilla ice cream, hulled strawberries, graham cracker crumbs, sugar, and vanilla extract into a blender.
02 - Blend on high speed until the mixture is completely smooth and creamy, stopping to scrape down the sides of the blender as needed.
03 - Taste the milkshake and add more sugar if a sweeter profile is desired, blending briefly to incorporate.
04 - Divide the milkshake evenly between two tall glasses.
05 - Top each glass with whipped cream, a sprinkle of graham cracker crumbs, and sliced strawberries. Serve immediately with a straw.