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
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 Cheese

Deliciously Chocolaty Sandwich Cookies

The texture of chocolate cookies with raspberry 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.)

If the 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 frosting fuses with the velvety dark chocolate of the cookies to create an irresistible chocolate-berry Valentine’s Day treat.

Valentine's Chocolate Sandwich Cookies with Raspberry Cream Cheese Filling

Chocolate Sandwich Cookies Serving Tips

  • Fill Just Before Serving. 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.
  • Store Cookies and Frosting Separately. 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.)

More Valentine’s Treats

Valentine's Chocolate Sandwich Cookies with Raspberry Cream Cheese
This 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?

Valentine's Chocolate Sandwich Cookies with Raspberry Cream Cheese Filling

Chocolate Sandwich Cookies with Raspberry Cream Cheese Frosting

Heart-shaped chocolate cookies filled with raspberry cream cheese frosting are the perfect Valentine's Day cookie and yummy enough to eat all year!

Prep: 45 mins
Cook: 9 mins
Total: 54 mins

Servings: 16 sandwich cookies, approx. depending upon the size of your cutter

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

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.

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Erin Clarke

Hi, I'm Erin Clarke, and I'm fearlessly dedicated to making healthy food that's affordable, easy-to-make, and best of all DELISH. I'm the author and recipe developer here at wellplated.com and of The Well Plated Cookbook. I adore both sweets and veggies, and I am on a mission to save you time and dishes. WELCOME!

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32 Comments

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  1. Your story is so dang cute. Lip smackers 4LYFE. AMEN!

    I wish we had this tradition. Someone sold roses for like 50cent, and boys bought them and sent them anonymously to girls they liked. The popular girls would go home carrying 2 dozen roses, and knock-kneed green bean pole me would go home with none. But my dad always bought me roses, so there! :)

    1. We had the exact same system in high school, and it was awful. It would get to the point where girls just started buying them for their friends, so that no one would be left out. I never thought that I would need a shiny foil balloon to feel secure, but boy was I grateful that we had that exchange system every Valentine’s Day!

  2. Awww that’s the cutest story ever!!! And these sandwich cookies are perfect :) Seriously I need to say this again, I love reading your posts!

  3. These are so cute! Loved your stories of middle school Valentine’s Day festivities, haha. You could definitely win over some people with these cookies. I love the chocolate and raspberry combo!

    1. Beth, I’m going to keep baking to win people over as long as I can get away with it! Happy Valentine’s Day to you :-)

  4. I totally forgot about the Valentine Mailbox in elementary school! Haha! I oh my gosh, I used up all the glitter and pom pom balls decorating mine. Would have definitely had a leg up with these cookie sandwiches. These look wonderful!

    1. POM POMS. I can’t believe I forgot about those! Those furry little guys would put anyone’s mailbox over-the-top. I bet you were the envy of every girl in your class Natalie.

  5. Cute…lol…I love MacGyver! As a kid, sometimes I made my valentines and sometimes it was equally fun buying them pre-made (depending what grade I was in). But either way I had to give one to every single person in the class! These cookies are goregous. :)

    1. Tina, we had to give them to everyone too! (I think this was a good thing.) I feel like as I got older I had ambitions to make them homemade, but it would be the night before and I would end up with the box, LOL. I should have just baked cookies instead!

    1. Thanks so much Teffy! Chocolate and raspberry are two of my favorite Valentine flavors, so I was excited to put them together.

  6. These are so pretty and cute for Valentine’s Day! Haha, I loved your story and your shiny foil box with hearts was genius! I would totally fill your box up with Tweety Bird Valentine’s if you filled mine with these chocolate raspberry cookies:)

  7. haha Dr. Pepper Lip Smackers – oh my gosh I totally forget about those (and all the other flavors obviously!). Were those the ones that you could string on a necklace?? I vaguely also remember something like that! ha! And these cookies are so so pretty! Love the color of that frosting!

  8. Tin foil? Nicely done Erin! :) Although I’d take a bowl of that frosting, even if I couldn’t apply my lip gloss in the reflection of it :) These cookies are so cute!

  9. Hahaha, I totally remember the stress of picking out valentines for each kid in class! Trying to pick JUST the right one for the boy you had a crush on – you didn’t want him to KNOW (heaven forbid), but you didn’t want him to think you thought he was gross, either. And heaven help you if you gave the gross nose-picker the good valentine! Oh, the stress.

  10. I would like to eat raspberry cream cheese frosting for ever and ever. Amen. That’s all. I can’t even focus on Valentines right now – my brain (and belly!) are craving frosting. yuuuummmm ….

    1. Gretchen, I may or may not have taken out a good chunk of the frosting with a spoon! It’s great on graham crackers too. Don’t ask me how I know…;-)