MAKE THE GANACHE
In a small sauce pan, heat the cream until it bubbles on the sides and just simmers.
Place the chocolate squares in a small bowl and pour the cream over the top. Let it sit for five minutes, then whisk together with a fork until smooth.
MAKE THE MILKSHAKES
In a medium sized bowl, place the cherries and pour the brandy on top. Toss the two items together and let them sit for at least 30 minutes.
Place the ice cream, the brandied cherries, the almond extract, honey and milk in a blender and process on high speed until smooth. Taste with a spoon to see if you'd like it a little sweeter (add more honey) or thinner (add more milk.)
In your serving glasses, divide the chocolate ganache on the bottom, and then pour the cherry milkshake over the top. Add about 1/3 cup of whipped topping to garnish, and another fresh cherry.
NOTE: I use coconut milk ice cream and regular cream to make this shake and it was delish. I add this note just in case you wonder about using a dairy alternative - it's totally fine and works great.