In a medium bowl, combine the graham cracker crumbs, melted butter, and granulated sugar until the crumbs are evenly coated and resemble wet sand.
Press the crust mixture firmly into the bottom of a 9x9-inch baking dish, creating an even layer. Place the dish in the refrigerator while preparing the filling.
In a large mixing bowl, beat the softened cream cheese until smooth and creamy with no lumps remaining. Add the powdered sugar and vanilla extract, mixing until fully combined.
Pour the heavy whipping cream into a separate chilled bowl and whip until stiff peaks form. This helps create the light and fluffy texture of the dessert.
Gently fold the whipped cream and whipped topping into the cream cheese mixture until smooth and airy.
Add the well-drained crushed pineapple and carefully fold it into the filling so the pineapple is evenly distributed throughout the mixture.
Spread the pineapple cream filling evenly over the chilled graham cracker crust using a spatula to smooth the top.
Sprinkle toasted coconut flakes over the top for extra flavor and texture. Add pineapple chunks and whipped cream if desired for garnish.
Cover the dessert tightly and refrigerate for at least 4 hours or overnight until fully chilled and set.
Slice into squares and serve cold for the best creamy texture and refreshing flavor.