Vanilla Cupcakes with Chewy Chocolate Chip Cookie Bottoms

Sometimes life is confusing.

Chewy Chocolate Chip Cookie Bottomed Vanilla Cupcakes

You know.

Do blueberries taste good in mojitos?

Wait, really… did I buy these skinny jeans?

Do people actually drink wine after squishing grapes with their toes? Seriously?

Chewy Chocolate Chip Cookie Bottomed Vanilla Cupcakes

What’s going to happen to Vincent Chase come September?

Do I want a cookie or a cupcake?

What was I thinking when I bought those jeans?

Can I have both a cookie and a cupcake?

How much longer must I ellipticize tomorrow if I have both a cookie and a cupcake? Or… two cookies. And a cupcake.

Why didn’t the sales associate warn me that these skinny jeans come with the Fat Booth app built in?

Chewy Chocolate Chip Cookie Bottomed Vanilla Cupcakes

Ahhh. Life is delightful.

Since I’m not ready to debate jeans that make you shimmy and shake or speculate about Vincent Chase’s fate, let’s talk about these cupcakes.

I love these cupcakes. They have a split personality: a chewy chocolate chip cookie base with a soft vanilla cupcake on top, crowned with generous frosting and sprinkles. I decorated them with colorful sprinkles in a casual, carefree way and pressed a chewy cookie piece into the frosting for extra indulgence. Yes, they definitely needed more calories — and I was more than happy to provide them.

These were made for thatguyIlivewith*, who promptly ate three after a well-balanced lunch of a double burger and a protein bar. He ate seven burgers that weekend, so I’m considering requesting a new life insurance policy for him.

Chewy Chocolate Chip Cookie Bottomed Vanilla Cupcakes

Chewy Chocolate Chip Cookie-Bottomed Cupcakes

Makes 18–20 cupcakes

Cookie layer:

  • 1/2 cup butter, softened
  • 3/4 cup brown sugar, loosely packed
  • 1 egg
  • 1 teaspoon vanilla extract
  • 1 1/3 cups all-purpose flour
  • 1 teaspoon baking soda
  • 1/4 teaspoon salt
  • 3/4 cup chocolate chips

Preheat the oven to 350°F. In a bowl, sift together the flour, baking soda, and salt. In the bowl of an electric mixer, beat the butter and brown sugar until light and fluffy. Add the egg and vanilla and beat until combined. Add the dry ingredients and mix until just combined, then fold in the chocolate chips.

Line a muffin tin with liners and lightly spray each with non-stick spray. Using a spoon also sprayed with non-stick spray, press about 1 1/2 tablespoons of cookie dough into the bottom of each liner.

Cake layer:

  • 1/2 cup butter
  • 1 cup white sugar
  • 2 whole eggs
  • 1 tablespoon vanilla extract
  • 1 1/2 cups flour
  • 1 teaspoon baking powder
  • 1/3 cup milk

Keep the oven at 350°F. In the mixer bowl, cream the butter and sugar until fluffy, about 3 minutes. Add the eggs and vanilla and beat until combined. In a separate bowl combine the flour and baking powder. Add half of the dry ingredients to the wet mixture and mix until just combined, then add the milk. Finally, add the remaining dry ingredients and mix until just combined.

Using an ice cream scoop or spoon, drop the batter on top of the cookie dough in each liner. Bake at 350°F for 15–18 minutes, or until a toothpick inserted into the cake portion comes out clean.

Top the cooled cupcakes with your favorite frosting, colorful sprinkles, and a chocolate chip cookie piece.

Note: A vanilla frosting recipe was used for these; for reference I doubled the cookie recipe above and baked the extra dough as cookies to place on top of the frosting.

Chewy Chocolate Chip Cookie Bottomed Vanilla Cupcakes

*Names have been changed to protect the innocent guilty.