From Kindergarten through fifth grade, Valentine’s Day incited a ferocious competition amongst the girls. If only I had been armed with two dozen Chocolate Sandwich Cookies with Raspberry Cream Cheese Frosting back in the day, I could have dominated.

Chocolate Sandwich Cookies with Raspberry Cream Cheese Frosting
Was our merciless girl-on-girl battle about to whom Billy gave the king-sized Kit Kat or whose scrunchie was the fiercest shade of pink? No. Was it over who had the widest assortment of Looney Tunes characters to pass out? Puh-lease. Bugs Bunny was out by third grade. No, the subject of our vicious female fight was in fact: whose Valentine’s Day “mailbox” was the shiniest, the sparkliest, and the most all-around reminiscent of an outfit Dolly Parton would wear to the Country Music Awards.

Did your middle school have this tradition? At Valentine’s Day, students were assigned to a) bring a Valentine for every student and b) Decorate a shoebox to act as a receptacle for valentines from other classmates. The boys brought brown paper lunch bags with hastily drawn hearts their mothers scribbled in ballpoint pen at school drop off, when they spied their sons’ classmates (girls) walking in with their perfect pink boxes. The girls, on the other hand, gave their mothers weeks notice and specific instructions to buy out the glitter section at Hobby Lobby. Heart stickers were for losers.

Valentine Chocolate Sandwich Cookies with Raspberry Cream Cheese Frosting

My mom wasn’t quite as obliging with the craft store runs, so I had to be a little more MacGyver with my shoebox decorating. My crowning year was fourth grade when I covered the entire shoebox in perfectly pleated tin foil, then taped bright red paper hearts all over the outside. I didn’t have glitter, but I had a box so mirror-like, the girls could use it to apply their Dr. Pepper Lip Smackers. For one day, I felt like The Queen Bee.

It would be a few years before I learned the real secret to self-esteem and validation: bake your way to popularity. One bite of these deeply chocolaty, lightly chewy, and luscious raspberry cream cheese frosting-stuffed Chocolate Sandwich Cookies, and the girls would have followed me anywhere, even if all I brought for my “mailbox” was a plastic Walmart sack. Chocolate Sandwich Cookies with Raspberry Cream Cheese Frosting are mesmerizing.Valentine Chocolate Sandwich Cookies with Raspberry Cream CheeseThe texture of Chocolate Sandwich Cookies with Raspberry Cream Cheese Frosting is a hybrid of a classic cutout cookie and a soft brownie. They are firm enough to hold their shape, yet soft enough to sink your teeth through easily. Ponder this cookie-brownie texture phenomenon whilst nibbling your third.

Chocolate Sandwich Cookies with Raspberry Cream Cheese Frosting are big and bold on the chocolate-flavor front. Not overly sweet with a powerful cocoa punch, these intensely chocolaty cookies remind me of the dark chocolate truffles I keep stashed in my desk in case of “emergency.” (Emergencies begin daily at 10 a.m.)
Valentine's Chocolate Sandwich Cookies with Raspberry Cream Cheese Filling
If Chocolate Sandwich Cookies teeter on the edge of being too chocolaty (does such a condition exist?), Raspberry Cream Cheese Frosting relieves us of our chocolate peril. The brightness and tang of the Raspberry Cream Cheese Frosting fuses with the velvety dark chocolate of the cookies to create an irresistible chocolate-berry Valentine’s Day treat.

Because the Raspberry Cream Cheese Frosting will become soft as it sits at room temperature (the cookie sandwiches might slide around a bit), I recommend filling the Chocolate Sandwich Cookies just before serving. The cookies and frosting will keep separately (cookies in an airtight container at room temperature; raspberry cream cheese frosting in the fridge) for about 10 days. (Note: check the shelf life of your cream cheese—you should only keep the frosting for that length of time.)
Valentine's Chocolate Sandwich Cookies with Raspberry Cream CheeseThis Valentine’s Day, I propose we bust out the glitter glue, draw sparkly hearts on shoe boxes, and give each other valentines. I promise to drop a few Chocolate Sandwich Cookies with Raspberry Cream Cheese Frosting inside of yours, if you’ll put a Looney Tunes valentine in mine. Deal?

Chocolate Sandwich Cookies with Raspberry Cream Cheese Frosting

Yield: 16 sandwich cookies, approx. depending upon the size of your cutter
Prep Time:
45 mins
Cook Time:
9 mins
Total Time:
54 mins
Heart-shaped chocolate cookies filled with raspberry cream cheese frosting are the perfect Valentine's Day cookie and yummy enough to eat all year!

Ingredients

For the Cookies:

  • 1 1/2 cups all-purpose flour
  • 3/4 cup unsweetened cocoa powder
  • 1 1/4 teaspoons baking powder
  • 1/4 teaspoon kosher salt
  • 3/4 cup unsalted butter, softened — (12 tablespoons)
  • 1 1/4 cups granulated sugar
  • 1 teaspoon pure vanilla extract
  • 1 large egg — at room temperature
  • 1 large egg yolk — at room temperature

For the Raspberry Cream Cheese Filling:

  • 4 ounces cream cheese — room temperature
  • 3 tablespoons unsalted butter — room temperature
  • 1/4 cup raspberry jam
  • 1/8 teaspoon almond extract
  • 1 drop red food coloring — optional
  • 1 3/4 cups powdered sugar

Instructions

  1. In a medium bowl, sift together the flour, cocoa, baking powder and kosher salt. Set aside.

  2. In a large bowl, cream together the butter and sugar until smooth. Beat in the vanilla, egg, and egg yolk. On low speed or by hand, gently stir the sifted ingredients into the butter-sugar mixture until they form a soft dough. Divide dough into 2 pieces, flatten each slightly into disks, and wrap tightly in plastic wrap. Refrigerate for 1 hour or overnight.

  3. When ready to bake, place rack in the center of the oven (or upper and lower thirds to bake two batches simultaneously) and preheat oven to 375 degrees F.

  4. Line baking sheets with parchment paper and set aside. On a lightly floured surface or between two sheets of wax paper, roll the dough out to a 1/4-inch in thickness. The dough will be sticky, so spread additional flour on the rolling surface as needed. Cut rolled dough into heart shapes with cookie cutters. Place cookies 1 1/2 inches apart on prepared baking sheets.

  5. Bake for 9 minutes, until just dry at the edges. If baking two sheets at once, rotate positions halfway through. Allow cookies to cool on baking sheet for 5 minutes, then remove to a wire rack to cool completely.

  6. Prepare Raspberry Cream Cheese Filling: Beat the cream cheese, butter and jam together until smooth. Beat in the almond extract and food coloring. Reduce speed to low, then sift in powdered sugar a little at a time. Once sugar is incorporated, increase mixer speed to high and beat until the mixture is smooth. Refrigerate filling until the cookies have completely cooled and are ready to be filled.

  7. Fill and assemble cookies: With an offset spatula or a piping bag, spread or pipe desired amount of filling on the back side of one cookie, leaving a small margin at the edges. Top with a second cookie to create a “sandwich.” Enjoy immediately.

Recipe Notes

  • The Raspberry Cream Cheese Frosting will become soft as it sits at room temperature, so fill just before serving. The cookies and frosting will keep separately (cookies in an airtight container at room temperature; raspberry cream cheese frosting in the fridge) for about 10 days.
Course: Dessert
Cuisine: American
Keyword: Chocolate Sandwich Cookies with Raspberry Cream Cheese Frosting, Easy Cookie Recipe

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PS. Tweety Bird is my favorite Looney Tunes valentine. Isn’t he everyone’s? I always felt like the Tasmanian Devils were reserved for the boys you didn’t want to risk thinking you had a crush on. The horror!

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