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Valentine Surprise Cookies

by Jessie Daye

First published: February 3, 2014 | Updated: June 10, 2026

Valentine’s Day is all about fancy dates, expensive dinners, and awkward surprises right!? Well these cookies are quite the gift. You can put messages inside them to your loved one …. like “Be Mine”, “Thinking of you”, even an engagement ring …. or a “Will you Mary Me?” …… or an anti-Valentine cookie with nothing inside …. OK, that was mean. Hah, but funny! Let your imagination run wild with these!

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Valentine Fortune Cookies

Makes (10) 3.5″ Surprise Heart Cookies

Ingredients
2 cups butter, softened
1 cup white sugar
2 tsp Vanilla extract
4 cups all-purpose flour
24oz milk chocolate (finely chopped or chips)

Valentine Fortune Cookies

Author: Jessie Daye
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Prep 1 hour 15 minutes
Cook 11 minutes
Total 1 hour 26 minutes
Heart-shaped surprise cookies with a hollow center filled with messages, candy, or small gifts, held together with tempered chocolate.
Servings 10 cookies

Ingredients

  • 2 cups butter, softened
  • 1 cup white sugar
  • 2 tsp vanilla extract
  • 4 cups all-purpose flour
  • 24 oz milk chocolate, finely chopped or chips

Method

  1. Cream butter and sugar until fluffy. Stir in vanilla; add flour and mix well. (add food coloring if desired to get colored dough)
  2. Separate dough into 2 halves and wrap in plastic wrap then refrigerate for 1 hour.
  3. Preheat oven to 350 degrees F (180 degrees C).
  4. Remove half the dough from the refrigerator and roll with a rolling pin until 1/4" thick. Using your 3.5" cookie cutter make 30 hearts.
  5. Using your 2.5" cookie cutter, cut out a smaller heart in the center of 10 of the large hearts. These will be your center cookies. All remaining 20 cookies will be your base and top. Place on a baking sheet lined with parchment paper. Bake for 10-12 minutes until very slightly browned.
  6. Once your cookies are cool, melt 1/2 your chocolate in a glass bowl at 30 second intervals, stirring in between, until chocolate is completely melted. Remove from the microwave and stir in remaining 1/2 of the chocolate chips. Stir to combine until all chocolate is completely melted. Pour 1/4 of the chocolate into a small piping bag with a tiny tip. Pipe a small amount of chocolate onto the BACK of the middle cookie and stick it to the top of the base cookie.
  7. Fill your cookie with candy hearts, sprinkles, little notes, or other fillings, and start piping a thin chocolate line on the top edge of the middle cookie.
  8. Take your third cookie (preferably the best looking one) and put it on top of the piped chocolate. Refrigerate for 2 minutes so everything is secure.
  9. Spread the remaining chocolate all over the top and sides of the cookie. Refrigerate for 5 minutes until firm. Enjoy!

Notes

This is a very delicious shortbread cookie recipe but if you have your favorite shortbread or butter cookie recipe that you love, by all means use it. You just need a semi-firm cookie recipe. You can fill cookies with candy hearts, sprinkles, little notes, or even small surprises like engagement rings and messages.

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Hi, I'm Jessie. 

I’m a Los Angeles mama, home renovator, and lifelong creative, sharing the things that make everyday life a little more beautiful. I believe food is one of the best ways to bring people together, which is why I love cooking: it turns an ordinary Tuesday into something worth remembering. From recipes I make on repeat to DIY projects, home design, and a little bit of real life in between — welcome to my corner of the internet. I’m so glad you’re here.

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