01 - Add the softened cream cheese, whole milk, vanilla ice cream, hulled strawberries, graham cracker crumbs, sugar, and vanilla extract to 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 shake and add more sugar if a sweeter profile is desired, then blend briefly to incorporate.
04 - Divide the milkshake evenly between two tall glasses.
05 - Finish each glass with a dollop of whipped cream, a sprinkle of graham cracker crumbs, and sliced strawberries if desired.
06 - Serve right away with a straw for the best texture and flavor.