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July 25, 2022

In late high school and early college, I held a string of random jobs: Skate School figure skating instructor, costumed cashier at a local Halloween store, dog walker, college entrance essay editor. But one of my absolute favorites was working front-of-house at Chili’s. 

While it wasn’t the pinnacle of a fine dining experience, it was (and is) also a very typical restaurant experience for most of America. This Chili’s sat in the shadow of a Costco, constructed between an Olive Garden and Longhorn Steakhouse.

The bartender who — despite his real name being something like Chad or Brian — went by Spike had been there the longest. He was tall, a little gangly and world-weary in a way that seemed more fitting for a dive bar owner than someone who served electric blue, sugar-rimmed margaritas to giddy suburban moms out for girls’ night.

He offered every new female employee the same bits of advice: If you’re kind to the back-of-house guys, they’ll keep you fed; never smile too much when you’re serving couples or you’ll risk making someone jealous; and always push the skillet cookies. 

While some may regard some of Spike’s advice as a little sexist, it definitely served me well — especially the skillet cookie bit. Those things were a home run. I’d watch as the cooks would drop oversized dollops of chocolate chip cookie dough into miniature greased cast iron skillets — the same kind from which the restaurant serves its queso — and toss them in the oven for 12 minutes or so. When they emerged, they were immediately topped with one scoop of vanilla ice cream and a drizzle of sticky-sweet chocolate syrup. 

On Friday and Saturday nights, especially, they sold like hotcakes. They ran about $6 at the time and were definitely large enough for two people to split, though there was something decadent about having one all to yourself. One of our regulars, a woman with a collection of Ann Taylor blazers that screamed “real estate agent” or “pharmaceutical rep,” would typically come in on Wednesday nights after the dinner rush and find a seat at the bar. 

She’d order a glass of red wine and a skillet cookie, then Spike would slide her the remote so she could find a hockey game. She was Canadian, we later found out. It seemed like a really cozy ritual, one I was thinking about recently after I stumbled upon a few 3.5-inch Lodge cast iron skillets at a resale store. 

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Initially, they were great for small-batch cooking — a single egg, some baked apples, etcetera — and just looking cute in my kitchen. But then a few Wednesdays ago, I realized I’d already had quite the week and the week wasn’t even over yet. To paraphrase food writer Bettina Makalintal, I deserved a little treat. 

So, I popped a little blob of frozen homemade cookie dough (thank you, Past Ashlie) into a skillet and let it bake until crisped around the edges and gooey in the center. I didn’t have ice cream or syrup, but I made do quite nicely with a frankly embarrassing amount of whipped cream. I skipped the wine and found some hockey. 

Since then, I’ve nailed down a version that works well in a standard 10-inch cast iron skillet, meaning there’s more than enough to share with friends.

Dark Chocolate Chunk Skillet Cookie


  • 6 tablespoons unsalted butter, softened 
  • 1/2 cup packed dark brown sugar 
  • 1/3 cup granulated sugar 
  • 2 large eggs
  • 2 teaspoons pure vanilla extract
  • 1 1/4 cup all-purpose flour
  • 1/2 teaspoon baking soda
  • 1 teaspoon Kosher salt 
  • 1 cup dark chocolate chunks


  1. Preheat the oven to 350 degrees. In a large bowl, combine the butter and sugars. Stir in the eggs and vanilla, followed by the flour, baking soda and salt. Finally, stir in the chocolate chunks.
  2. Transfer the cookie dough to a 10-inch cast iron skillet. Smooth the dough with the back of a spoon to ensure it’s even across the skillet.
  3. Bake just until the edges are golden-brown, 18 to 20 minutes. Allow to completely cool before topping with too much whipped cream. 

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