Description

This Strawberry Banana Pudding is a luscious layered dessert combining macerated strawberries, ripe bananas, creamy homemade whipped topping, and smooth vanilla pudding. Featuring a perfect balance of fresh fruit and indulgent creamy layers with a cookie base for a delightful texture contrast, it’s easy to assemble and best enjoyed chilled after a few hours to allow flavors to meld and cookies to soften.

Ingredients

Fruit

16 ounces strawberries, rinsed and sliced
6-8 ripe bananas, sliced and sprinkled with a little fruit preserver or lemon juice

Syrup & Sweeteners

½ cup granulated sugar
2-3 tablespoons strawberry syrup (reserved from macerated strawberries)

Dairy & Cream

2 cups heavy whipping cream
3-4 tablespoons powdered sugar
1 teaspoon vanilla extract (for whipped cream)
8 ounces cream cheese, room temperature
14 ounce can sweetened condensed milk
2 cups cold milk (whole milk or unsweetened almond/oat milk)

Dry Ingredients

2 3.4-ounce boxes Instant Pudding (French Vanilla or Vanilla flavor)

Flavoring

1 teaspoon vanilla bean paste or vanilla extract (for pudding mixture)

Cookies

3 packages Chessmen cookies or similar

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Instructions

Macerate Strawberries: Place sliced strawberries and granulated sugar in a bowl, toss well to coat. Let them sit on the counter for 30-60 minutes so the berries release their syrup and become nicely macerated.
Prepare Pudding Mixture: In a mixing bowl, combine cold milk, instant pudding mix, and vanilla bean paste (or extract). Whisk with a hand mixer until smooth. Set aside to thicken while preparing other components.
Make Homemade Whipped Cream: Whip heavy cream until soft peaks form, then add powdered sugar and vanilla extract. Continue whipping until stiff peaks develop. Refrigerate until ready to fold into the pudding mixture.
Combine Cream Cheese Mixture: In another bowl, beat the softened cream cheese, sweetened condensed milk, and 2-3 tablespoons of the strawberry syrup until smooth using a hand mixer. Gently fold the homemade whipped cream into this mixture, followed by folding in the thickened pudding mixture, stirring carefully until fully blended.
Layer the Dessert: In a 13x9-inch dish, lay a base layer of Chessmen cookies. Top with half the sliced bananas, then half the macerated strawberries (drain strawberries, reserve syrup in the fridge). Spread half of the pudding mixture over the fruit.
Repeat Layers: Add another layer of cookies, followed by the remaining bananas and strawberries. Cover evenly with the remaining pudding mixture. Top the final layer with the last package of Chessmen cookies.
Chill Before Serving: Cover the assembled pudding with plastic wrap and refrigerate for at least 1 hour and up to 24 hours. The ideal chilling time is about 4 hours to allow the cookies to soften and flavors to meld. The dessert may be eaten immediately but the texture will be firmer.
Serve: Optionally garnish with fresh sliced strawberries and drizzle with the reserved strawberry syrup for added flavor and presentation before serving.

Notes

Use fruit preserver or a splash of lemon juice on banana slices to prevent browning.
If using store-bought whipped topping instead of homemade whipped cream, use approximately 12 ounces thawed.
The dessert benefits from chilling time for best flavor and texture; immediate serving is possible but cookies will be firm.
French Vanilla or Vanilla instant pudding mix are both suitable; avoid flavored variations to keep classic taste.
Chessmen cookies provide a nice crunch and absorb moisture well; substitute with similar butter cookies if necessary.