01 - Place whole milk, softened cream cheese, vanilla ice cream, hulled strawberries, granulated sugar, and vanilla extract into blender canister.
02 - Blend on high speed until completely smooth and creamy, stopping to scrape down sides of blender as needed for even consistency.
03 - Taste mixture and add additional sugar if desired, blending briefly to incorporate.
04 - Divide milkshake evenly between two chilled glasses.
05 - Top with whipped cream, crushed graham crackers, and fresh strawberry slices as desired.
06 - Serve promptly with straws while shake remains thick and cold.