Place the strawberries in a tightly covered container and freeze.
When the strawberries are rock hard, place three milkshake glasses in the freezer. Leave for ten minutes.
Make the ganache by heating the chocolate and cream in the microwave, on HIGH, for about 30 seconds. Stir until smooth.
Take the glasses out of the freezer and drizzle some of the ganache down the sides--inside the glasses, NOT outside.
Dump the frozen strawberries, ice cream, milk and quarter cup of sugar into the blender. Process until smooth. Taste and add the rest of the sugar, if needed. Pulse a couple of times to blend in the added sugar.
Pour the milkshake into the prepared glasses.
Top each glass of milkshake with a scoop of vanilla ice cream.
Dip the whole strawberries in the remaining chocolate and press into the ice cream.
Drizzle the rest of the ganache over the milkshake.
Serve the old-fashioned strawberry milkshake at once.