01 - Add whole milk, softened cream cheese, vanilla ice cream, fresh strawberries, granulated sugar, and vanilla extract to a blender container.
02 - Blend on high speed until completely smooth and creamy, stopping to scrape down the sides of the blender as needed to ensure even incorporation.
03 - Taste the milkshake and add additional sugar if desired, blending briefly to incorporate any adjustments.
04 - Pour the finished milkshake evenly into two chilled glasses, filling them near the top to allow room for garnishes.
05 - Top each glass with whipped cream, a sprinkle of crushed graham crackers, and fresh strawberry slices if desired.
06 - Serve the milkshakes promptly with straws while cold and at optimal consistency.