Hull 4 strawberries and cut in half. Smash strawberries with a fork and place in a small saucepan over low heat. Add 1 tablespoon sugar to the pan. Simmer for 5 minutes, stirring occasionally.
While the strawberry puree is simmering & waffles are toasting - Using a KitchenAid stand mixer or handheld electric mixer, whisk together ⅓ c heavy whipping cream, 2 tablespoon cream cheese, 1 tablespoon sugar, and ¼ teaspoon vanilla extract until firm peaks.
Warm up 1 tablespoon Nutella in microwave for 40 seconds.
Drizzle Nutella over warm waffles, top with strawberry puree & whipped cream, and garnish with additional cut strawberries & confectioners sugar. Enjoy!