colander set over a bowl. Let it drain for at least 10–15 minutes, pressing gently with the back of a spoon to remove as much excess juice as possible. The drier the pineapple, the thicker your dip will be.
Place the softened cream cheese in a medium mixing bowl. Using a hand mixer (or a sturdy wooden spoon if you don’t mind a little workout), beat the cream cheese until it is smooth, fluffy, and free of lumps.
Add the powdered sugar to the cream cheese. Beat on low speed at first so the sugar doesn’t puff everywhere, then increase to medium and mix until the sugar is fully incorporated and the mixture is silky and creamy.
Fold the well-drained crushed pineapple into the sweetened cream cheese mixture using a spatula or spoon. Stir until the pineapple is evenly distributed and you see little golden flecks throughout the dip. Taste