Combine strawberries, sugar, and water in a medium pot and bring to a simmer over medium heat. As it simmers, lightly mash the strawberries and cook for 6-8 minutes until it thickens a bit, then let cool to around room temperature.
For chocolate ganache:
Combine ingredients in a metal mixing bowl and place over a small pot with simmering water. Stir the chocolate until it melts evenly with the butter. If the mixture gets too thick, use a little more milk to thin it. When chocolate is even, drizzle into serving glasses or use to dip strawberries in.
For whipped cream:
Combine ingredients in a medium bowl and whisk like crazy until it holds stiff peaks. Chill until needed.
To make milkshake:
Add ice cream, milk, cocoa powder, and strawberry syrup in a blender (you’ll have some syrup left). Pulse until smooth. Pour milkshakes into chocolate-drizzled glasses and top with whipped cream. Garnish with cherry or chocolate covered strawberries.