Pulse strawberries until chopped into small pieces, but not completely blended.
Transfer to a bowl and stir the 2 tablespoons sugar into the mixture.
Let rest until macerated, about 30 minutes. Strawberries should be very soft and surrounded by liquid.
To make the merry cream, add mascarpone, whipping cream, 1 teaspoon sugar, and ½ teaspoon vanilla extract to a large mixing bowl or the base of a stand mixer.
Whisk by hand or with stand mixer until soft peaks form. Set aside.
To make the blended cream base, add 1 cup ice, milk, ½ teaspoon vanilla extract, and ice cream to a blender.
Blend until very smooth, about 35 seconds.
Divide the blended cream between two glasses.
Top with macerated strawberries.
Top with a dollop of merry cream and (if desired) sprinkle with red sanding sugar just before serving.