01 - Place milk, softened 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 needed to ensure even incorporation.
03 - Taste the milkshake and add additional sugar if needed, blending briefly to incorporate.
04 - Pour the blended milkshake evenly into two chilled glasses.
05 - Top each glass with whipped cream, crushed graham crackers, and fresh strawberry slices if desired.
06 - Serve the milkshake promptly with straws while cold and at optimal consistency.