Prepare chocolate pastry cream up to one day ahead of time; it will need at least an hour in the fridge to cool down. You can also make storebought chocolate pudding here to make it even easier! Prepare vanilla cookies with enough time to let them cool down (about 1 hour before assembly!) Skip this step if using storebought cookies. Prepare raspberry sauce by combining fresh or frozen raspberries, sugar, and lemon juice in a small saucepan. Cook over medium to low heat until the raspberries break apart, about 5-10 minutes; it doesn't need to be very thick! Let cool for about 30 minutes in the fridge.
Whip the cream until it reaches stiff peaks (you can add 2 tsp sugar and a splash of vanilla extract for additional flavor!)
To begin assembly, you will need two medium sized glasses (we used tulip beer glasses for this, which do hold a pint of liquid; you can also use 4 smaller glasses or one large serving dish, but the amounts listed below are for 2 medium sized glasses! Feel free to adjust accordingly!)
Add 2-3 tablespoons of chocolate pastry cream.
Crumble 3 vanilla cookies on top of the pastry cream.
Layer 2 tsp of raspberry sauce on top of the cookies.
Arrange 8-9 raspberries around the edge of the glass.
Add about 2 tbsp of the heavy whipping cream.
Crumble 2 cookies on top of the cream.
Add 2-3 tablespoons of chocolate pastry cream.
Layer 2 tsp of raspberry sauce on top.
Add another 5 fresh raspberries on top. We added a thin layer of whipped cream below, but this is optional!
Pipe about 2-3 tbsp of whipped cream on top using a star nozzle (this is optional, you can just spoon the cream on top as well!)
Optional: shave chocolate on top for additional decoration.
Repeat the layering process with the second glass - you can make this dessert ahead of time and keep in the fridge for a few hours before serving! Enjoy!