Before getting started, chill your milkshake glasses in the freezer for at least 10 minutes before making the recipe.
Start by washing your fresh strawberries in a large bowl, and then pat them dry with paper towels or on a tea towel.*
Once they're good and dry, cut off the strawberry tops, and slice the strawberries into halves with a paring knife before adding to the blender jar.
Once you've got all your strawberries sliced up, go ahead and add them to your blender jar with the vanilla ice cream and the milk.
Blend for ten to twelve seconds, 'til everything is well combined. You can add more ice cream for a thicker texture, or more milk for a thinner texture, pulsing a few times after each addition until you've reached the desired consistency.
Finally, pour your homemade strawberry milkshake into your frozen milkshake glasses, and top it off with a big dollop of whipped cream and a fresh strawberry, and serve!