Project Description

“I like redheads. Their mouths are like a drop of strawberry jam in a glass of milk.” – Roger Sterling (about Joan)

I love that quote. I think the writers give Roger all of the best mildly inappropriate one-liners. Like, “when God closes a door, he opens a dress.” Oh Roger. 

Image from

You scoundrel, you.

His quote inspired me to make a thumbprint cookie in a heart shape with strawberry jam and a pale cookie base. They have a nice, delicate crispiness to them, but are still chewy. Vanilla bean in the cookie base makes for  a powerful flavor boost! With the fun heart shape, these are also perfect for Valentine’s Day!

Speaking of…how to make that distinctive heart shape, you ask? I imagine you could use your pinkie finger and wing it, but I’m a bit more exact than that. And, I have a husband who humors me and is always looking for an excuse to use his workbench in the garage. So, he made me this:

Pretty, it is not. He explained his choice of medium, mainly because it was food/water safe. I stop listening when he gets technical, so I don’t remember much more than that. He loves me anyway though. Here is what the cookie look like stamped:

If you don’t have a handy husband or simply aren’t a crazy perfectionist like myself, you can use your finger or anything heart shaped to create the indention. It will spread anyway, so that will help hide any imperfections!

Joan’s Heart Thumbprint Cookies

Recipe Type: Drop Cookies
Author: Jennifer
Serves: 18
Vanilla bean cookies with a heart-shaped strawberry jam center. Perfect for Valentine’s Day!
  • 1 3/4 cup all-purpose flour
  • 1/2 teaspoon baking powder
  • 1/2 teaspoon salt
  • 3/4 cup unsalted, softened butter
  • 2/3 cup white sugar, plus additional for coating
  • 1 egg
  • 1/2 of a vanilla bean, seeds scraped from the pod, or 1 teaspoons of vanilla extract
  • 1/3 cup seedless strawberry jam
  1. Preheat the oven to 350 degrees. Line cookie sheets with parchment paper. Whisk the flour, baking powder, and salt together in a small bowl. Set aside.
  2. Beat the butter and sugar together for about 5 minutes. The batter will become very pale. Beat in the egg and vanilla seeds/extract. Slowly add in the dry ingredients, mixing until just combined. At this point, I chilled the batter because I wasn’t going to bake the cookies that day. The dough was relatively soft, so you may want to chill it for a bit in the fridge.
  3. Make 1 inch balls of dough and roll in white sugar and place on cookie sheet. Using a heart-shaped tool or your finger, create the heart shape. Repeat for all of your dough balls.
  4. Fill each cookie with 1/2 to 3/4 teaspoon of jam. I used a ziploc bag with the corner cut to pipe the jam into the cookies. It worked well for me and I just tried not to fill them too much.
  5. Chill the cookies in the freezer for about 5-10 minutes. My cookies still spread a bit, but miraculously, I had no jam spillage, which is a common complaint with thumbprint cookies. I can’t definitively say it was because of the freezer time, but it couldn’t hurt to try it out.
  6. Bake your cookies for about 15-17 minutes, until edges are golden brown.

Adapted from Food Network Kitchens


Find more Mad Men inspired treats here