Soak the pineapple rings: Begin by soaking the 8 pineapple rings in a mixture of 1 cup dark rum and 1 cup coconut rum for at least 1 hour. After soaking, drain the rings and pat them dry with paper towels to remove excess liquid.
Set up the dredging station: Prepare three bowls: Place 1.5 cups flour in one bowl, in a second bowl whisk together 2 large eggs and 1/2 cup coconut milk, and in the third bowl, have 10 oz sweetened coconut flakes ready.
Heat the oil: In a large, deep skillet, pour enough vegetable oil to be about 1 inch deep. Heat the oil over medium-high heat until shimmering.
Dredge the pineapple rings: Take each pineapple ring and first coat it in the flour, then dip it into the egg and coconut milk mixture, allowing any excess to drip off. Finally, press the ring into the coconut flakes to ensure a robust coating.
Fry the rings: Carefully place the coated pineapple rings into the hot oil. Fry for about 1 minute on each side, or until they turn a beautiful golden brown. Once fried, remove the rings and drain them on paper towels to absorb excess oil.
Make the cream cheese dip: In a mixing bowl, combine 4 oz cream cheese and 1/2 cup powdered sugar. Mix until smooth; then stir in additional dark or coconut rum to taste, enhancing the dip's tropical flavor.
Serve warm: Enjoy the crispy pineapple rings warm, served alongside the rum-infused cream cheese dip.