Remove cream cheese from refrigerator and let it soften at room temperature for at least 2 hours before making the dip. If you forgot to soften it ahead of time, cut the cream cheese into smaller cubes to help it blend more easily.

In a large mixing bowl, combine the softened cream cheese using an electric mixer. Beat until smooth and creamy, scraping down the sides of the bowl as needed. The whipped cream cheese variety works exceptionally well for extra fluffiness.

Gradually add the cup of sugar to the cream cheese mixture. Continue beating until well combined and the mixture becomes even creamier. The sugar will help achieve the perfect consistency while adding the signature sweetness.

Thoroughly drain the crushed pineapple using a fine mesh strainer or colander. Press the pineapple with the back of a spoon to remove as much juice as possible. This step is crucial to prevent the dip from becoming watery.

Add the well-drained crushed pineapple to the cream cheese mixture. Using a rubber spatula, gently fold the pineapple into the mixture until evenly distributed throughout.

Grate the mild cheddar cheese if you haven’t already. Add 1½ cups of freshly grated cheddar cheese to the mixture and fold in gently until combined. Fresh grating provides better texture than pre-shredded cheese.

Give the dip a final gentle stir to ensure all ingredients are well incorporated. Taste and adjust sweetness if desired, though the recipe is perfectly balanced as written.

Transfer the dip to a attractive serving bowl. Chill for 30 minutes if desired, though it can be served immediately. Present with an assortment of crackers for the authentic Brenda Gantt experience.