Chocolate Valentine Cookies (2024)

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My mom and I used to make these together every Valentine’s Day, and the recipients ranged from cute little girlfriends in the more innocent early adolescent years, to (much to my mom’s consternation) full-on polo shirt-and-Topsider-wearing boyfriends later in high school. They’re sweet little chocolate heart cookies, personalized with stencils and sifted powder sugar, which couldn’t be an easier decorating method.

I used to go nutso with the suckers, spelling out Valentine heart quotes such as “Be Mine” and “Love You” and “You’re Cute”

My mom nixed “Kiss Me,” unfortunately. What a buzzkill she was! I’d also spell out names, the date of that Valentine’s Day, and would occasionally cut my own geometric stencils and make funky designs on the cookies for some interesting decoration. It really is a fun way to decorate.

You’ll want to have tweezers to remove the stencils once the powdered sugar has been dusted on, and might also need a fine brush of some kind to erase mistakes. Other than that, you just need a heart cookie cutter and some alphabet stencils that fit the cutter. Easy and fun to make with kids.

And—sigh—so romantic.

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Begin by adding 2 sticks of unsalted butter to the bowl of an electric mixer. I’m almost exclusively a salted butter gal, but in this case, unsalted butter is necessary.

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Cream the butter until fluffy, then add in the brown sugar.

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Cream that mixture, then add in one egg…

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And some vanilla…

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And mix until totally combined.

Into a separate bowl, mix add flour, salt, baking powder, cinnamon, and cocoa powder.

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Whisk it together to combine.

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Then add it in two batches to the butter/sugar mixture in the mixing bowl, mixing well after each addition.

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Next—and this is important—do not eat all of this dough. If you do eat all of this dough, you will not have any cookies.

This has been a public service announcement.

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Stick the dough into a large Ziploc bag, then flatten it into a disc. This’ll make it easier to roll out later.

Now just throw it into the fridge for a couple of hours.

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While the dough is chilling, find your heart cutter…or cutters! This was a heart cutter nesting set I picked up a few months ago.

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When you’re ready to make the cookies, remove the dough from the fridge. Remove it from the plastic bag and set it on a lightly floured surface. You’ll need to let it sit for maybe five to ten minute, just to soften enough to make it easy to roll out. If it cracks violently when you first start to roll it, wait a few more minutes.

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Before you cut the cookies…

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Make sure the stencils you’re going to use will fit the size of the heart.

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Then roll out the dough on a lightly floured surface, cut them out, and place them on a piece of waxed paper or a baking mat. Don’t roll the dough too thin; I prefer the cookies to be a little on the soft side, and if you roll them too thin, they’ll be crisp and tragic.

Bake them for about 12 minutes or so, then let them cool completely.

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When you’re ready to decorate, lay the stencil right on top of the cookie.

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Cut up pieces of scrap paper and lay them over any areas of the cookie that are exposed.

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Then lightly sift powdered sugar over the top. As you can see, I wasn’t very “light” with my sifting because I evidently had some kind of muscle spasm.

Don’t be like me.

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Use (clean) tweezers to carefully lift off the paper and stencil, being very careful not to drop powdered sugar as you remove them.

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There you go! As you can see, I could have gone a little lighter with the powdered sugar, as it looks like it’s going to have an avalanche here in a second. But you get the idea.

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This one’s a little better. Not so clumpy.

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Finish up with all the letters you need, then arrange them on a pretty napkin on top of a tray.

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Oh, and you can also do inverse stencils for a different look (and for more powdered sugar per cookie.)

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Nice!

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Make these for your sweetie on V-Day. Spell out his/her name, cute V-Day sayings, or decorate them in pretty patterns. Have fun with them!

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And if you have any leftover cookies…

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Chocolate icing…or, in my case, Nutella.

Amen.

Lots of Love,
Pioneer Woman

Here’s the handy printable:

Chocolate Valentine Cookies (2024)
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