Drain crushed pineapple extremely well using a strainer or clean hands
Add softened cream cheese to a bowl and mix until smooth
Stir in mayonnaise until fully combined
Add shredded cheddar cheese and mix gently
Stir in chopped onion, sugar, salt, and black pepper
Fold in the drained pineapple until just combined
Cover and refrigerate for at least 30 minutes
Stir once before serving
Notes
Draining the pineapple thoroughly is essential to prevent a watery dipUse sharp cheddar for the best balance of sweet and savoryFinely chop the onion so it blends without overpoweringChilling allows flavors to mellow and improves textureBest served with crackers, pretzels, or celeryStore covered in the refrigerator for up to 3 days