01 - Add milk, softened cream cheese, vanilla ice cream, hulled strawberries, granulated sugar, and vanilla extract to blender container.
02 - Blend on high speed until completely smooth and creamy, stopping to scrape down sides of blender as needed.
03 - Taste milkshake and add additional sugar if desired, blending briefly to incorporate.
04 - Pour into two chilled glasses. Top with whipped cream, crushed graham crackers, and fresh strawberry slices. Serve immediately.