Valentine's Day Gooey Broken Heart Cookies

Have a broken heart this Valentine's Day and need a delicious pick-me-up treat? Invite your single friends over to help you indulge in an ooey, gooey candy-filled heart that will lift your spirits, soothe your soul and satisfy your sweet tooth.
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  • Level: Intermediate
  • Total: 4 hr 30 min (includes chilling time)
  • Active: 1 hr
  • Yield: 10 sandwich cookies
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Ingredients

2 cups all-purpose flour, plus more for dusting (see Cook's Note)

1/8 teaspoon baking soda  

3/4 teaspoon fine salt  

1 large egg 

1 teaspoon pure vanilla extract  

1 1/2 sticks (12 tablespoons) unsalted butter, at room temperature  

1/2 cup granulated sugar  

1/4 cup confectioners' sugar, plus more for dusting 

20 caramel and milk chocolate candies, such as Rolos 

Pink gel food coloring 

Directions

  1. Whisk the flour, baking soda and salt together in a medium bowl. Beat the egg and vanilla together in a small bowl.
  2. Beat the butter, granulated sugar and confectioners' sugar together in a large bowl with an electric mixer on low speed. Once incorporated, increase the speed to medium and beat until slightly creamy, about 3 minutes. Stop and scrape down the sides of the bowl with a rubber spatula as needed.  
  3. Reduce the speed to low. Slowly pour in the egg mixture and beat until combined. Add the flour mixture in 3 additions, increasing the speed as the dough gets thicker to keep the beaters spinning. Scrape down the sides of the bowl and the beaters as needed. Once all the flour is just incorporated, tint the dough to desired color by adding a few drops of food coloring and mixing to combine. Then increase the speed to medium-high and beat until the dough is very smooth, about 5 minutes. 
  4. Turn the dough out of the bowl onto a clean work surface and bring it together into a ball. Divide into 2 even pieces. Shape each piece into a flat square and wrap in plastic wrap. Refrigerate the dough for at least 3 hours or up to 24 hours.  
  5. While the dough is chilling, quarter each of the caramel candies and place in a small bowl. Refrigerate until ready to use.  
  6. When ready to roll, cut and bake the cookies, position racks in the upper and lower thirds of the oven and preheat to 350 degrees F. Line 2 baking sheets with parchment.  
  7. Dust another sheet of parchment with flour and put 1 piece of the dough on top. Dust with more flour and top with another sheet of parchment. Roll the dough out between the parchment sheets to about 1/4-inch thick (and about 11 by 9 inches) and place in the freezer until slightly chilled, about 5 minutes. Repeat with the remaining piece of dough.  
  8. Cut out cookies with a 3-inch heart-shape cutter and arrange 5 cookies on each of the prepared baking sheets, about 1 1/2 inches apart, for 10 cookies total. Place a heaping tablespoon of the cut caramel candies in the middle of each heart in one layer, leaving the edges of the cookie clean. Gather the scraps of dough, then roll out and cut in the same manner until you have 10 more hearts (do not put candy on top of these). Place one of these heart cookies on top of each of the 10 cookies on the baking sheets and press gently around the edges to seal . Freeze until very firm, about 20 minutes.  
  9. Bake, rotating the baking sheets front to back and bottom to top about halfway through, until the cookies are golden brown around the edges, 16 to 18 minutes. Let cool on the baking sheets on a wire rack, about 5 minutes. Transfer cookies to the rack to cool completely. Dust with confectioners' sugar before serving. 

Cook’s Note

When measuring flour, we spoon it into a dry measuring cup and level off excess. (Scooping directly from the bag compacts the flour, resulting in dry baked goods.)