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Homemade Cookies & Cream Pudding Cups

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February 04, 2016 · 2k Views

(Jennie is a guest blogger from One Sweet Mess.)

These Cookies & Cream Pudding Cups are every chocolate lover’s dream, and they’re just in time for your Valentine’s Day celebrations.

Chocolate is, and always has been, the Valentine’s Day mascot. It’s what everyone wants and craves, which is why you see it lining the shelves of almost every store that sells food. I’m not a fan of playing Russian roulette when it comes to my chocolate, which is why I tend to stray away from the multitudes of chocolate boxes that make their yearly appearance right before Valentine’s Day.

I prefer to know exactly what it is I’m stuffing into my mouth rather than risk having to spit the mystery subject out because it was stuffed with something the color of gangrene. I’m sure most of you have had the same unfortunate experience.

There’s no mystery when it comes to pudding. These Cookies & Cream Pudding Cups are made with an easy-to-make homemade chocolate pudding recipe that gets layered with Oreo cookie crumbles and topped with homemade vanilla bean whipped cream. If you can operate a whisk, then you can make this recipe (it’s that easy). If you want to drop a step and make this recipe even easier to whip up, you can use store-bought whipped cream instead. Either way, these pudding cups are delicious.

Servings: 4



  • 2 tablespoons granulated sugar
  • 2 tablespoons cornstarch
  • 2 tablespoons cocoa powder
  • Pinch of salt
  • 1 and ½ cups whole or 2% milk
  • ¾ cup heavy cream
  • 4 ounces semi-sweet chocolate, chopped
  • ½ teaspoon vanilla extract
  • ½ teaspoon coffee extract
  • 10 chocolate sandwich cookies, crumbled

Whipped Cream:

  • 1/2 cup heavy cream
  • 2 tablespoons powdered sugar
  • ½ teaspoon vanilla bean paste


  1. To make the pudding, add sugar, cornstarch, cocoa powder, and salt to a medium saucepan. Gradually whisk in the milk and cream until combined. Bring the mixture to a gentle boil over medium-high heat, whisking constantly. Allow the mixture to boil until the pudding thickens, about 2 minutes. Remove from the heat and whisk in the chocolate, vanilla and coffee extracts. Continue to whisk until the chocolate is melted and the pudding is smooth.
  2. Transfer the pudding to medium bowl. Place a piece of plastic wrap directly on top of the warm pudding mixture to prevent a skim from forming. Refrigerate for at least 4 hours or overnight.
  3. To make the whipped cream, add the cream to the bowl of a stand mixer fitted with a whisk attachment (or using a handheld electric mixer), beat cream on medium-high. As the cream thickens, add the powdered sugar and vanilla bean paste. Continue to beat until soft peaks form.
  4. To assemble the pudding cups, layer 2 tablespoons of pudding in the bottom of a small glass mason jar. Top with 1 tablespoon of the cookie crumbles. Add another 2 tablespoons of pudding and an additional 1-tablespoon of cookie crumbles to the jar. Top with a dollop of whipped cream and a sprinkle of the cookie crumbles. Continue with the remaining three mason jars. Serve immediately.

Notes: If you don’t have coffee extract handy, you can add 1 teaspoon of instant coffee or espresso powder to the pot with the dry ingredients. Or, you can replace the coffee extract with an additional ½-teaspoon of vanilla extract.

Four ounces of semi-sweet chocolate chips will also work in the recipe.

If you don’t have vanilla bean paste handy for the whipped cream, you can substitute ½-teaspoon of vanilla extract.

I prefer to assemble the pudding cups directly before serving so the cookies remain crunchy. You can make the cups up ahead of time and keep them stored in the refrigerator, but the cookies will become soft.


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Jennie Phaneuf is the baker, photographer, recipe developer, and mess-maker behind One Sweet Mess. Making a mess in the kitchen is highly encouraged and licking the spatula is an absolute must. In her world, cookies are a nutritional breakfast option, sprinkles taste good on just about everything, and sangria is best served daily.
dtran5Feb 04, 2016
yumm! Looks delicious. I love homemade whipped cream!

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