In honor of Valentines day I wanted to make heart shaped cookies. I attempted to mold the cookie dough, but honestly they ended up looking like little penis cookies, which I guess could be entertaining and follow some theme on the "love holiday." In the end I just decided on normal round cookies, but theses cookies are far from normal. In lieu of my beau's love of cinnamon and cookies, I wanted to make these cinnamon roll chocolate chip cookies in hope of winning his heart again and again through his stomach. I mean my mother always told me a way to a man's heart is through his stomach and never accept a ring unless it's in a blue box with a white ribbon. Whether celebrating Valentines with a special someone or watching porn while eating cheez-whiz on crackers and crying on the inside, these cookies are a perfect way to warm anyone's heart and make you feel a little bit better.

Cinnamon Roll Chocolate Chip Cookies


24 cookies

Adapted from: Bakingdom


  • 1 1/4 sticks of melted butter
  • 3/4 cup of brown sugar
  • 1/2 cup of granulated sugar
  • 1 egg
  • 1 egg yolk
  • 2 teaspoons of vanilla extract
  • 1/2 teaspoon of baking soda
  • 1/2 teaspoon salt 1 1/2 cups of flour
  • 1 cup of chocolate chips
  • For the filling:
  • 1/4 stick of butter melted
  • 1/2 tablespoon ground cinnamon
  • 1/2 cup sugar 1/4 + 1/8 cup flour


  1. Combine the butter and the sugars. Then add in the vanilla and eggs. Next mix in the baking soda and salt. In small batches add in the flour. Lastly stir in the chocolate chips. Set the cookie dough aside. In a small bowl combine the melted butter, cinnamon, sugar, and flour. Add more sugar and flour if needed in order to reach a clumpy consistency. Lay out a piece of plastic wrap and spread the cookie dough out in a rectangular shape. Spread the cinnamon filling in the middle of the cookie dough. Using the help of the plastic roll up the cookie dough into a log. Place the log into the fridge for at least one hour. Preheat the oven to 350 degrees. Line a baking sheet with parchment paper. Take the cookie dough out of the fridge. Slice the dough in 1/2 inch thick rounds. Place the dough into the oven for 8-10 minutes, until the cookies are golden brown. Allow to the cookies to slightly cool and then move to a wire rack for them to fully cool.