Put frozen strawberries in a microwave-safe bowl, and microwave until thawed, about 25 seconds. Do not drain excess liquid. Set aside.
Pour 1 1/2 tablespoons of chocolate syrup into the waffle bowl, tilting the bowl from side to side so the syrup coats as much of the inside as possible (sides too!). Freeze for 30 minutes, or until syrup has solidified.
To the bowl of strawberries, add preserves and mash with a fork, until you have a chunky strawberry sauce.
Remove waffle bowl from the freezer and place in a dish. Scoop ice cream into the waffle bowl. Top with strawberry sauce and 1/2 tablespoon of chocolate syrup, and then finish it all off with raspberries and whipped topping. Enjoy!