01 - Add milk, cream cheese, vanilla ice cream, strawberries, sugar, and vanilla extract to blender jar.
02 - Blend on high speed until completely smooth and creamy, stopping to scrape down sides of blender as needed.
03 - Taste the mixture and add additional sugar if more sweetness is desired, blending briefly to incorporate.
04 - Pour milkshake evenly into two chilled serving glasses.
05 - Top with whipped cream, crushed graham crackers, and fresh strawberry slices if using.
06 - Serve right away with straws while milkshake is thick and cold.