Cakespy: Conversation Heart Cream Pie


Quirky, cute, sometimes controversial, always delicious recipes from Jessie Oleson.

Cakespy: Conversation Heart Cream Pie
  • Yield:8
  • Rated: 5.0

[Photographs and original illustrations: Cakespy]

Jessie Oleson (aka Cakespy) drops by every Monday to share a delicious dessert recipe. —The Mgmt.

I'm pretty sure that I can count on on hand the number of people who genuinely love the taste of Conversation Hearts. And that's when I think really hard.

Conversation Heart Cream Pie, however, is a different story.

Believe it or not, letting those sugary-chalky lumps steep in milk before making a cream pie custard filling actually does yield a surprisingly toothsome (if slightly tooth-decaying) pastry product. No, it's not fine dining—it's best described as vanilla cream pudding pie punctuated with melty, pastel sugar cubes—but it goes down much easier than you'd think, especially when crowned with a cloud of freshly whipped cream.

About the author: Jessie Oleson is a Seattle-based writer, illustrator, gallery owner, and cake anthropologist who runs Cakespy, an award-winning dessert website. She is currently at work on her first book.


  • 1 pre-baked pie shell, cooled
  • 2 cups cold milk
  • 1/2 cup Conversation Hearts, divided
  • 1 package (3.9 ounces) instant vanilla pudding


  1. 1.

    Put your pre-baked pie shell in the refrigerator. You'll leave it here for about an hour, to chill out while you prepare the filling.

  2. 2.

    Pour your 2 cups of milk into a bowl. Add 1/4 cup conversation hearts to the bowl, and put in the fridge to "steep" for about an hour.

  3. 3.

    Mix the "steeped" milk mixture with the instant pudding, whisking until it starts to thicken. You will have little pastel lumps of conversation heart in the mixture--they will not be all the way melted.

  4. 4.

    Pour the pudding into the prepared pie shell. Let set in the refrigerator for about an hour; garnish with whipped cream and the remaining conversation hearts directly before serving.

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