Chocolate Sandwich Cookies with Raspberry Cream Cheese Frosting

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?

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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!


Yield: about 16 sandwich cookies, depending upon the size of your cutter

Total Time: 2 hours (includes cooling time)

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 (12 tablespoons) unsalted butter, softened

  • 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


Directions:

All images and text ©Erin Clarke/Well Plated.

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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!

More Valentine’s Treats:

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About Erin Clarke

I’m fearlessly dedicated to making healthy food taste incredible. Wearer of plaid, travel enthusiast, and firmly convinced that sweets and veggies both deserve a place at the table. MORE ABOUT ERIN…

32 comments

  1. These are so cute and perfect to give that crush in your life! ;) hehe

  2. 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! :)

    • 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!

  3. 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!

  4. Cute, cute,cute! I am super crazy for Raspberry and Chocolate so this is PERFECT!

  5. Love these simple yet beautiful sandwich cookies, Erin. They are perfect for the VDay or everyday!

  6. 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!

  7. 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!

    • 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.

  8. 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. :)

    • 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!

  9. Those look so so sweet!!
    Perfect for Valentine’s day =)

    {Teffy’s Perks} X

  10. These look absolutely perfect for Valentines day. Chocolate and raspberry cream cheese…yum!

  11. 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:)

  12. 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!

  13. These are so adorable! I love them!

  14. 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!

  15. ahhh lip smackers! i remember those! :) what a fabulous cookie.

  16. These look absolutely delicious!

  17. 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.

  18. These are adorable treats! What are you and your hubby’s plans for valentines day?

    Alicia
    http://www.healthingyou.com

  19. 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 ….

  20. These are SO cute! I love sandwhich cookies!

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