Peanut Butter & Jelly Chocolate Whoopie Pies

Peanut Butter & Jelly Chocolate Whoopie Pies

Peanut Butter & Jelly Chocolate Whoopie Pies


I have mentioned more than once that generally speaking, I don’t care for peanut butter. never have, never will. Strangely, while five of my six kids like peanut butter, one of my sons has never liked it either. That is so weird to me! You don’t think of food liking as being in any way genetic, but with six kids, I have learned that they really do seem to be in some cases. That same son hated bananas for many years. His father, whom he hadn’t lived with since an extremely young age, also hated bananas. Go figure.

But every once in a while, I get a strange (strange because well… I don’t LIKE pb so it’s akin to a rabid vegetarian suddenly craving steak tartare) craving for something peanut buttery. Usually I just have a peanut butter sandwich and that’s that; I’m done for 6 months or so. But today I was working on a blog post anyway. It was supposed to be chocolate whoopie pies with chocolate filling (I hear some of you sobbing out there because I changed it lol) but the peanut butter and jelly sandwich craving hit (twice a year, like clockwork 😛 ) and my 4 watt mental light bulb went off and I thought to myself “self ( I call myself self when I’m not calling myself somewhat obscene names), why not make a peanut butter filling for these instead?! The you can use that bag of mini reeses cups you bought and never ate!” Then I had another flash of brilliance and decided to add some raspberry jam in them pies. Raspberry goes well in PB&J sandwiches and it definitely goes well with chocolate so… voila, Peanut Butter & Jelly Chocolate Whoopie Pies were born. Well, born in my household anyway. I’m sure that at some point they were born somewhere else already lol.

I then congratulated myself for being a genius, made myself a cup of tea and had some chocolate as a reward for being so brilliant and got started. The end result is pretty yummy if I do say so myself. Mind you, my whoopie pies aren’t flat and tiny like most. Why you ask? Because I’m lazy. It was much easier to put the cookie batter in my muffin top pan than to spoon out each individual cookie and make sure it was shaped nicely. The benefits of this is that you also get these cool crispy edges as well as some HUGE arse whoopie pies hehe. But I will write the directions as written in the cookbook (aptly called “Whoopie Pies” by Sarah Billingsly). Just know that you CAN do these in a muffin top pan too. You’ll just get less but bigger pies and they will be thicker.

You know the drill… get to cookin’!

Peanut Butter & Jelly Chocolate Whoopie Pies

  • Whoopie Pie-
  • 1 2/3 cup flour
  • 2/3 cup unsweetened cocoa powder
  • 1 1/2 teaspoons baking soda
  • 1/2 teaspoon salt
  • 4 tablespoons butter, room temp
  • 4 tablespoon shortening, room temp
  • 1 cup dark brown sugar, firmly packed
  • 1 egg
  • 1 teaspoon vanilla extract
  • 1 1/4 cup milk
  • Peanut Butter Filling-
  • 3/4 cup peanut butter (I used crunchy)
  • 6 tablespoons unsalted butter, room temp
  • 3/4 cup powdered sugar
  • about 1/3 cup raspberry jam (or whatever flavor you prefer)
  • 1 2.5 ounce bag mini Reeses Peanut Butter Cups (find at the check out lanes in the grocery store), each cup cut in half
  1. Preheat the oven to 375. Line 2 baking sheets with parchment paper.
  2. Sift together the flour, cocoa powder, baking soda and salt onto a large piece of waxed paper.
  3. In the bowl of a stand mixer (can use a hand mixer if you need to),  beat the butter, brown sugar and shortening on low speed until combined. Scrape down the sides of the bowl, increase the speed to medium and beat for about 2 minutes until smooth and creamy.
  4. Add the egg and vanilla extract and beat on low speed just until combined. Turn off and scrape down the bowl again. Add half of the flour mixture and half of the milk and beat on low until combined. Add the remainder of the flour and milk and again, beat on low until just combined.
  5. Spoon batter, about a tablespoon at a time, onto the prepared baking sheets. Bake for about 10 minutes at 375 degrees or until the cookies spring back when touched gently. Let them cool on the pan for about 5 minutes, then remove to a rack to cool completely.
  6. Make your filling- In a medium bowl, combine the peanut butter and butter. Beat at medium speed until smooth & creamy. Add in the powdered sugar and beat on low until combined, then turn the mixer up to medium and continue beating until it is creamy and fluffy looking.
  7. Fold in the chopped reeses cups.
  8. Spread a good sized dollop of the peanut butter filling on the flat side of half of the cooled cookies. Top with another good sized dollop of jam. Top each cookie with another of the unfilled cookies, flat side inwards. Magically, your cookies are no longer just cookies, but are now Whoopie Pies. Enjoy!! 🙂

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7 thoughts on “Peanut Butter & Jelly Chocolate Whoopie Pies

    • So all this time all I had to do was feed you something PB&J!? Damn, woman, you coulda told me you were so easy. I never would have bothered with the Mercedes and the diamonds!

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