Romantic Chocolate Covered Cherry Whoopie Pies

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While a red velvet whoopie pie for Valentine’s Day would certainly suffice for a little dessert romance, I couldn’t help but think outside the food coloring on this one. This Valentine’s Day you can not only impress your special someone with a semi-homemade treat but have a little fun with him too!

One of my favorite romance friendly desserts includes anything and everything that needs to be dipped. You can still with a fondue pot and some of your favorite meats and dipping sauces then follow it up with a chocolate fondue to dip pound cake and fruits … like cherries. Pair those with these chocolate covered cherry whoopie pies and you’ll find the way to your man’s heart … through his stomach.


Cherry Buttercream Filling

  • 1/2 cup vegetable shortening
  • 1 stick butter
  • 3/4 cup cherry pie filling, pureed
  • 4 cups powdered sugar

Whoopie Cakes

  • 1 box Chocolate Fudge cake mix
  • 3 eggs
  • 1 1/4 cup water
  • 1/3 cup vegetable oil
  • 1 – 4 serving box instant Chocolate Fudge Pudding mix

Tools Needed



  1. Preheat oven to 350 degrees F and spray whoopie pie pan with Wilton cake release spray.
  2. In an electric mixer on a low speed, combine eggs, water, oil.
  3. Add pudding mix and cake mix.
  4. Continue to beat on medium speed for 2 minutes, until smooth.
  5. Using a spoon, place a large dollop of cake batter into each heart and spread evenly with the smooth side of the spoon.
  6. Bake 6 – 8 minutes, until a toothpick comes out clean when placed in the center of a whoopie cake.
  7. Allow to cool completely before frosting.
  8. In an electric mixer, combine shortening and butter on high speed until mixed well.
  9. Add pureed cherry sauce and mix on a medium speed for 30 seconds.
  10. Add powdered sugar 1 cup at a time and mix for 1 minute until smooth.
  11. Using a disposable piping bag, pipe frosting between two layers of whoopie cakes.


Disclosure – As a Wilton Brand Ambassador I was provided with product. Opinions expressed are my own and are not influenced by monetary compensation.


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  1. OMG these sound sooooooo good!

  2. Forget sharing – I want those for myself :) Yum!

  3. Those look delicious! They’re adorable too – even better!

  4. Those look great!
    I didn’t even know there was a whoopie pie pan.
    I have a whoopie pie cookbook, they all taste good but they’re all round – none look this good.

  5. Forget Valentine’s Day, I would make those all the time! So pretty!

  6. Okay, I didn’t realize you could get heart shaped whoopie pie pans. How cool is that?

    These really look AH-MAY-ZING. So delicious. My mouth is pretty much watering.

  7. Oh yum, they sound yummy! The cream sounds delicious!

  8. Oh YUM YUM YUM!! Those look amazing!

  9. Virginia says:

    My husband would love that filling. He loves the whole theme of Chocolate Covered Cherry stuff. I was not sure how to contact you privately, but may I ask how you became a Wilton Ambassedor.


  10. Those are so cute! I am really wanting a heart shape tin now!

  11. Ohh I love anything chocolate and cherry. These are gorgeous!

  12. Virginia says:

    So i wanted to let you know that I kinda made these. LOL. I told my husband about them and he thought they sounded awesome. I did a scratch Whoopie pie cake and in a traditional round shape because well I work as a WMI and I spend too much money on product already. LOL. But then I made the buttercream exactly how you said, but my husband felt it needed more cherry, so I used a whole can of cherry pie filling, and did not buzz all of it, just the first part, the rest I added into the KA and so it left slightly bigger little chunks of cherry. My only complaint was by adding that much cherry the buttercream started to break and could have used probably a cup more powdered sugar to help with that. Otherwise the combination is awesome. I am wondering if yours has enough cherry because you are using a cake mix to make the whoopie and my cakes were a really dark chocolate, so it was a bit harder to get the cherry to come out so I add the rest. Either way thanks for the awesome idea, hubby said these are not one of his favorite things and he had never had a whoopie pie before.

    • Yeah I probably should have mentioned it’s a subtle cherry flavor, just because it’s my preference. My husband added a dollop of the pie filling right from the can to the center of his to get a more rich flavor.

  13. OK, THOSE freaking rock! I mean, HELLO!!! C-H-O-C-O-L-A-T-E!!! Once again, excellent work Cat. Love the Chocolate Covered Cherries too! :)

  14. These are SO cool! How fun! And of course, CHOCOLATE is my favorite!!! DUH!!! Excellent work Cat!!!

  15. Heavenly!

  16. That looks DELISH!!! I have never had one!


  1. […] The majority of Americans probably don’t care where the whoopie pie originated as long as they can eat one. Looking to make something beyond the original? CakeSpy has a very inventive recipe for her Elvis Peanut Butter Whoopie Pie, and Oh My! Sugar High has a more romantic recipe for Chocolate Covered Cherry Whoopie Pies. […]