We Made a Creamy Pineapple Squares Recipe from 1968—and It’s Ready for a Comeback

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This recipe for Creamy Pineapple Squares might be retro, but tropical flavors never go out of style.

It’s impossible for us to resist retro recipes from the ’60s. You can’t go wrong with homemade meatloaf, beef Wellington or any recipe inspired by Julia Child. But when we saw this Creamy Pineapple Squares recipe in The 1968 Jell-O Pudding Ideabook, we couldn’t help but wonder if this no-bake Jell-O dessert would still be a showstopper on today’s table.

How to Make Creamy Pineapple Squares

Creamy Pineapple Squares begin with an easy press-in graham cracker crust, mixed with chopped toasted walnuts for extra flavor and crunch. Next, Jell-O boxed pudding mix is prepared with pineapple juice and milk instead of water, and blended with cream cheese to make it ultra-rich.

Ingredients

Creamy Pineapple Squares ingredients laid out on a wood cutting board surfaceAllison Robicelli for Taste of Home

  • 3/4 cup graham cracker crumbs
  • 2 tablespoons sugar
  • 1/3 cup chopped toasted walnuts
  • 2 tablespoons butter, melted

Filling:

  • 1 package Jell-O Vanilla or Coconut Cream Pudding & Pie Filling
  • 1 cup canned pineapple juice
  • 1 cup milk
  • 1/4 cup sugar
  • 1 package (8 ounces) cream cheese, cut into cubes

Tools You’ll Need

Directions

Step 1: Make crumb crust

Combine graham cracker crumbs, sugar, walnuts and melted butter until the mixture resembles wet sand.

Step 2: Prepare the pan

Creamy Pineapple Squares step 2Allison Robicelli for Taste of Home

Press 2/3 of the mixture into an 8-in. square pan. (For easy removal, line the bottom and sides of the pan with parchment paper or aluminum foil first.) Set the remaining graham cracker mixture aside.

Step 3: Mix the filling ingredients

Creamy Pineapple Squares step 3: mix the filling ingredientsAllison Robicelli for Taste of Home

In a large saucepan, whisk together the Jell-O pudding mix with half the pineapple juice until smooth; whisk in the remaining pineapple juice, milk and sugar, then add the cream cheese.

Step 4: Cook the pineapple pudding

Cook the mixture over medium heat while whisking constantly until it comes to a full boil. Remove from heat and, using either a whisk or a handheld electric mixer, beat the pudding until completely smooth. It’s a workout!

Step 5: Assemble the dessert

Creamy Pineapple Squares fully assembled in the panAllison Robicelli for Taste of Home

Slowly pour the pineapple filling over the prepared graham cracker crust, gently shaking the pan to help it settle in an even layer. Sprinkle the remaining graham cracker crumb mixture over the top.

Step 6: Cover, chill and serve

Cover and chill for at least two hours until fully set. Cut the dessert into nine squares and serve.

Here’s What I Thought

Creamy Pineapple Squares finished product on white plate sitting atop a retro tableclothAllison Robicelli for Taste of Home

Based on taste alone, this recipe was a knockout: creamy, coconutty and irresistible. However, there were a few hiccups in the execution, thanks to the fact that Jell-O pudding packages are slightly smaller than they were back in 1968. This didn’t negatively affect the flavor at all, but as far as texture goes, Creamy Pineapple Squares were way too wobbly to work in an 8×8-in. square baking pan.

This is not an insurmountable problem, though. In lieu of making this Creamy Pineapple Squares recipe in a baking pan, I recommend making this dessert in individual ramekins. Though the original recipe is meant to be cut into nine portions, there is no harm in increasing the serving size to fit a standard 6-piece ramekin set.

If you’d prefer to make Creamy Pineapple Squares in a pan, I suggest freezing it before cutting into squares, then letting those squares thaw in the refrigerator before serving. Alternately, you can boost the jelling power of the pudding mix by adding 3/4 teaspoon unflavored gelatin.

How to Make This Recipe Your Own

Another great thing I realized about this recipe: It’s easy to tweak to make any number of amazing desserts:

  • To amp up the tropical flavor, replace the milk with coconut milk, and replace the walnuts in the crust with macadamia nuts or shredded sweetened coconut.
  • The pineapple juice can be swapped with peach nectar, orange juice or any other fruit juice.
  • To make Creamy Pina Colada bars, replace 1-2 tablespoons of the milk with dark rum.

Once you’ve got the recipe down, feel free to let your imagination run wild!

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Allison Robicelli
Allison Robicelli is a James Beard-nominated food and recipe writer, humorist, and the author of four (quite good) books. Her writing credits include the Washington Post, Bon Appetit, Food & Wine, Wine Enthusiast, Eater, Food52, The Takeout, and other major publications. Before becoming a full-time writer, she spent over a decade as a working chef, and was the co-owner of the acclaimed Robicelli's Bakery in Brooklyn, NY. In addition to food and comedy, she also writes about history, parenting, and cannabis. She lives in Baltimore, MD with her husband, two teenage sons, and four patient cats.