Step 1

Oil a grill pan or cast iron skillet and heat over medium-high heat.

Step 2

Once the pan is hot, place a few pineapple slices in at a time. Cook the pineapple slices without flipping or moving them at all until they are lightly browned (and have grill marks, if using the grill pan), about 3-4 minutes. Flip the pineapple slices over and continue to cook until browned on the other side. Set the cooked pineapple aside on a plate and continue until all of the pineapple has been browned.

Step 3

Reduce heat to medium. Without cleaning the pan out, add in the bacon, a few slices at a time. Cook, flipping once, until crisp but not burnt. Transfer cooked bacon strips to a paper towel lined plate to absorb excess grease.

Step 4

Chop up the bacon and pineapple into bite-sized pieces. Preheat the oven to 350°F.

Step 5

Pour off most of the bacon grease from the pan, leaving just a bit for cooking the garlic and habanero. Cook the garlic and habanero until fragrant, about 30 seconds. Stir in the cream cheese and mayonnaise. Allow the cream cheese to melt, and then add in the seasonings. Stir until evenly distributed. Do the same with the bacon, pineapple, and green onion, reserving a bit of each for topping. Mix in half of the shredded cheeses and smooth the dip mixture evenly into the pan. Top with the remaining shredded cheeses.

Step 6

Transfer the dip to the oven and bake until all of the cheese on top is melted and beginning to bubble, about 10 minutes. Top with the reserved bacon and pineapple and continue to bake, until lightly browned and bubbly, about 10 more minutes. Sprinkle with the remaining green onion and serve warm with chips, crackers, pita bread, or pretzels, to dip.