In a blender, combine ice cream, milk, strawberries, and sugar, and blend until well-combined and pourable.
Pour into a glass, top with whipped cream, and enjoy.
*If using frozen strawberries, allow your ice cream to sit at room temperature for 5 to 10 minutes before using, until it just begins to melt. Otherwise, you might have trouble getting everything to blend.*Use 1/2 cup milk for a thicker shake, up to 3/4 cup for a thinner, more sippable one.*If you prefer a less-sweet shake or are using extremely ripe berries, you can omit the sugar, but I recommend using it since cold ingredients mute sweetness.Approximate nutritional information is for 2 servings without optional whipped cream.