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Conversation Heart Cookies

A few days ago the devastating news broke that conversation heart candies will no longer be sold in stores. Hold on one sweet minute America! You can’t just rip a holiday classic right out of the world. Are we going to take away candy canes at Christmas too? Candy corns at Halloween? You better not even touch Peeps at Easter cruel world. How will we ever celebrate Valentine’s Day without those sassy sweet little hearts? Just kidding. I mean did anybody actually eat them? Not to mention the confusion they left after eating one “Hug Me” heart only to pull out a “No Way” the next heart. Talk about mixed signals. I prefer holiday staples in the form of sugar cookies anyway. And with that dramatic entrance out of the way…let’s chat about this week’s cookie tutorial conversation heart cookies! All the sweet + sass, way less dental work.

Conversation Heart Cookies - TutorialConversation heart cookies are typically a yearly must for every cookier but I haven’t made a set in a few years. (I’m sure I don’t have to remind you about my love for foods in disguise, do I?) I felt it was time for an update which gave me the perfect chance to play with a cookie stenciling technique I’ve been wanting to try. Screen printed stenciling. In a nutshell, a stencil is cut from vinyl, transferred to silkscreen, and then placed over the cookie. Icing or airbrushing is then applied just like a plastic stencil and removed leaving only the design. And the typical stencil design bridges? (The little pieces that have to connect everything together in a plastic stencil.) Screen printing eliminates them + gets nice and snug right up against the cookie allowing for super clean lines and no back spray! Hooray!

Conversation Heart Cookies - Tutorial

So I busted out my silkscreen, iron on vinyl, and designed a bunch of sassy in love sayings in Silhouette Design Studio and got to work. The result was AWESOME! I was hooked. Except for one little thing, the vinyl made it almost impossible for me to line up the text right where I want it because I couldn’t see through it. And that’s when it occurred to me….why not use CLEAR vinyl! Bam. Crisp clean stencil line perfection! Lined up properly and so darn easy.  I’m working on a full Silk Screen 101 post for you guys to give you lots more silk screening details including how I made my own silk screen frame (spoiler alert IKEA frame + silkscreen + hot glue). But I wanted you to be able to grab this stencil download and create some conversation heart cookies of your own right away. So let’s make some conversation heart cookies!



For personal use only.


  • heart cutter (I printed this one with my Silhouette Alta!)
  • icing bottles/piping bags + #2 tips
  • icing scribe
  • fan
  • 110 silkscreen mesh
  • clear vinyl or crafting vinyl
  • transfer tape
  • airbrush


  • 20-second icing in pastel pink, yellow, orange, blue, purple, and green (color formulas listed below)
  • red airbrush color


Note: It’s hard to calculate exactly how much coloring to use as a “drop” will vary from person to person. However, the following will give you an idea of about what it takes + color ratio. I like to color my icing the day before as it will often develop a share of two overnight. Go light on the coloring especially with these pastel colors. It helps to first drop your gel color onto the spatula first just in case. I always err on the side of less because it’s easy to add more. But if you do overdo it, you can always add more white icing to lighten it up.

  • pastel pink – 8 drops Americolor deep pink + 2 drops Americolor ivory + toothpick tip worth of  Americolor regal purple
  • pastel orange – 6 drops Americolor orange + 2 drops lemon yellow
  • pastel yellow – 6 drops Americolor lemon yellow
  • pastel green –  4 drops Americolor mint green
  • pastel blue –  4 drops Americolor sky blue
  • purple – 6 drops Americolor regal purple + 2 drops Americolor deep pink

Naturally, you’ll first need to bake your heart cookies + flood with 20-second icing in pretty conversation heart cookie pastels. The hearts I used were 3 inches wide at the widest spot and will fit the stencil file perfectly as is. However, the size of the stencil can easily be adjusted to fit your cookies in your cutting software. If you’d like to try my cookie recipe you can find that here and my icing recipe here.

Now let’s take a close look at to use these fancy new stencils!

Conversation Heart Cookies - Tutorial

Step 1: Resize your stencils to fit your cookies, if needed, in your cutting machines software, I’m using Silhouette Design Studio. Make sure to adjust your machine’s settings to vinyl. For me, it was a 3 on my blade. Cut out your stencils. I did so with my Silhouette Cameo. Next, you’ll need to weed the stencils. This means you want to remove the parts of the stencil you want icing or color to seep through. In this case, it is all of the letters except for the negative space inside letters like B or 0.  In the above image, I showed an example in blue so you could see it well. You’ll also want to cut around each stencil separately so they are no longer on one big sheet. Place transfer tape over the stencil (still on its backing) and press really well on the vinyl backing side of the stencil. Slowly remove the white backing from the vinyl being super gentle near the tiny negative letter spaces.

Step 2: Now lay the stencil sticky side down right on your silkscreen. Press and rub really well on the silkscreen side, then flip over and very gently remove the transfer tape. Sometimes the little pieces of the letters stay on the transfer tape. Just grab a pair of tweezers and place then back in the design, no biggie! Press on your newly made stencil really well to make sure it’s nice and stuck.

What you see in the pictures above is a simple DIY silk screen frame. Using just a piece of silkscreen and holding the stencil to the cookie works but the little frame was a game changer! I simply took a cheap Ikea frame (that happened to be about 1.4in tall inside the same as my cookies), removed all of the parts and hot glued silk screen tightly to the inside of the frame. Perfect and free! You can make the stencil just on silkscreen no problem, but I highly recommend this. The silkscreen lays just snug across the cookie.

Step 3: Lay your new stencil across you a cookie (using a frame or simply holding on to it) arrange it where you want it and airbrush red.

Step 4: Gently lift up and fall in love! I even found if I didn’t use quite enough red I could line it right back up and add more. So simple guys.

Whew guys! That was a lot of info. But that’s the story of how I made these conversation heart cookies and fell in love with silkscreen stencils at the same time. Stay tuned for the uber cute box details!


Heads up! To keep those legal gurus of the world happy, I need to inform you that some of the links in this post are affiliate links. In short – I may earn a small commission from the use of said link with no cost to you. But don’t worry I only link to stuff I use, love, and know you will too!

Image of Toni Miller in front of a sprinkle shelf.


 I’m Toni, the baker, the blogger,  and cookie cutter maker  behind The Sprinkle Factory and I hope you find a sprinkle of inspiration here at The Factory.

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