01 - Place milk, cream cheese, vanilla ice cream, strawberries, sugar, and vanilla extract into a blender canister.
02 - Blend on high speed until completely smooth and creamy, stopping to scrape down sides of blender as necessary.
03 - Taste the milkshake and add additional sugar if more sweetness is desired.
04 - Pour the blended mixture evenly into two chilled glasses.
05 - Top with whipped cream, crushed graham crackers, and fresh strawberry slices as desired.
06 - Serve immediately with straws while cold.