Deep Dish Caramel Stuffed Chocolate Chip Cookies

The other day, I went to a cookie exchange at my friend Erin’s house. It’s been a tradition for a couple of years now, and I always look forward to seeing the friends I went to school with for 12 years before heading off to college. Not to mention it’s a mother-daughter event, so we all have a great time laughing at all their antics (too much wine) and grimacing when they unblushingly tell all of our embarrassing stories (again, I blame the wine).

Even though I’ve grown up with these girls, I can’t help but want to show off when it comes to bringing the most extravagant cookies and usually like to experiment with a few showcase cookies that can’t help but look and taste delicious!

I’d like to take a second to address the massacre that occurred on Friday at Sandy Hook Elementary in Connecticut, and the blogging day of silence.

What happened at Sandy Hook was horrific. Just hearing the news and reading the stories sent chills of pain and fear down my spine.. and I’m across the country in the comfort of my own home. I cannot even begin to imagine the palpable fear among the hallways, the seizing terror that coursed through each person in every classroom. My aches are pale in comparison to the pain that must be wracking through every individual affected by this enormous tragedy.

For me, life is all about balance and I truly believe that a completely healthy life depends on both your mental sanity and feeling good in your own skin. Yes, I exercise and eat healthy, but I have absolutely no desire to live a life that consists of restricting and overexercising in the name of your health. If I want to eat a cookie, I’m going to eat it. If I want to take a week off from the gym because I’m not feeling too well, I’m going to do so without any regret whatsoever.

I know this sounds a little off tangent for a cookie post, but I sometime feel that “healthy living bloggers” get themselves stuck in a negative place when it comes to food and exercise and try to put forth a perfect picture of their life and body image. While Apple of My Eye usually concentrates on healthier recipes, I don’t want to restrict my site to any one genre. How boring would that be?

On Saturday, I had planned to post a recipe, but given the tragic incident on Friday, a recipe about bars seemed frivolous and insensitive. I opted to postpone my post on Saturday as a day to send positive thoughts toward Connecticut, and spend time with my family.

Many bloggers have decided to make today, Monday, a day of silence to honor and remember the lives lost on Friday. I whole-heartedly respect this decision. I believe death–even in these gruesome, heartbreaking circumstances–is handled differently by each individual. Some need lots of time to reflect and mourn, others would prefer life to continue on as they learn to heal their wounds day-by-day.

While I have never dealt with a loss of this magnitude, I am the type of person who prefers not to dwell on what happened, but embrace the people who were affected. These children were all loving, innocent souls. To see through their eyes would be seeing the world from a completely pure, imaginative perspective that we seem to lose as adults. A world of wonder and magic. A youthful, silly, happy world. A world of a kid.


  • 17 tablespoons butter
  • 1 cup granulated sugar
  • 1/2 cup packed brown sugar
  • 2 teaspoons vanilla
  • 2 tablespoons real maple syrup
  • 2 eggs
  • 2 3/4 cup flour
  • 1 teaspoon baking soda
  • 1/2 teaspoon salt
  • 1 cup chocolate chunks (I chopped up a large piece of Scharffen Berger chocolate – yum)
  • 1/2 cup milk chocolate chips
  • 1/2 cup caramel pieces (like this)
  • 3 tablespoons heavy whipping cream
  • coarse sea salt to taste


  1. Preheat the oven to 350 degree. Soften the 9 tablespoons butter in the microwave for 30 seconds or until partially melted. Soften the remaining 8 tablespoons for 10 seconds or until you can make an indent with your finger.
  2. Mix the butter and sugars together with an electric mixer until creamed. Add the vanilla and maple syrup and mix again until smooth. Add the eggs; beat slowly until incorporated. Add the flour, baking soda, and salt (sometimes it helps to add the flour in batches). Mix until a smooth dough forms. The dough should feel dry to the touch – if it sticks to your hands, add a few more tablespoons of flour. I generally try to err on the side of more flour. Stir in the chocolate chips and chocolate chunks. Melt the caramel pieces and heavy cream in the microwave for 2 minutes. Stir well until melted and smooth.
  3. Press half of the dough mixture into a 9-inch or larger cast iron skillet lined with parchment paper. Pour the caramel over the dough and smooth with a spoon. Cover with another layer of cookie dough. Bake for 15-25 minutes (see notes). Remove from oven, sprinkle with sea salt, and allow to rest for at least one hour in order for the pieces to hold their shape when cut.


  • I baked mine uncovered for 15 minutes, but you could also cover with foil and bake for an additional 10-15 minutes to get the cookie center baked even further. If you only bake for 15 minutes total, like I did, the cookie WILL be underbaked. Cause that’s how we like it.

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