← Back to Blog

Caramel-Stuffed Chocolate Chip Cookie Cups — The Ones Lily Brought to the Last Cookout

One week. The packing is done. The bags are in the entryway. The passports are in my carry-on with a backup color photocopy in the suitcase. The last few errands: Mai's prescriptions filled for thirty days, a small gift for the inevitable hospitality I expect at the cemetery groundskeeper or wherever, a stack of small bills (Vietnamese dong), and a bottle of Maker's Mark I bought for the gift to anyone we might find who knew Mai's family. Maker's Mark in Houston. Maker's Mark on the boats. Maker's Mark, the bourbon I gave up on March 14, 2009, but which is the right gift for a Vietnamese household, which Mai confirmed.

I went to my Tuesday AA meeting at the church in Bellaire. I told the group I would be away for two weeks. They asked where. I said, "Vietnam. With my mother." Bill — eighty-three years old now, my old sponsor, still attending every Tuesday — stood up and said, "Bobby, we'll be here when you get back. Don't drink in Vietnam." The room laughed. I said, "I won't." It wasn't funny but it also was. I have not had the urge to drink in years. But the joke is the joke. Sobriety is humor in there. The seriousness is in the silences.

Made cháo tôm for dinner Wednesday — the comfort meal. Smokey at my feet. The kitchen quiet. Smokey will be staying with Lily and James for the two weeks. He has been over there twice already to pre-acclimate. They have a small condo but a fenced patio and Smokey is a small dog and they will love him for two weeks and then he'll be glad to see me. Smokey is forty pounds of routine-loving brindle. He does not understand "vacation." He will understand. The dog is learning the family.

Last cookout Sunday before the trip. Sixteen people. Smaller than usual. I told them this might be the last cookout for a while — two weeks gone, plus a week to recover, plus jet lag — so I wanted to do it well. Smoked a brisket. Did the spring rolls. James brought jollof. Lily brought the cookies. Mai stayed home — she's saving her energy for the flights. Mr. Washington came over. He said, "Bobby, you give Vietnam my regards." I said, "Will do, Mr. Washington." He said, "And bring back a story." I will. I will bring back many stories. The stories are the whole point.

Lily didn’t ask what to bring — she just showed up Sunday with a pan of these, and they were gone before the brisket platter was even cleared. I asked her afterward what the recipe was, because that’s the kind of thing you want to be able to make yourself when you get back from two weeks away and you need something warm and a little indulgent to ease back into ordinary life. She texted it to me on the drive home. I’m putting it here so I don’t lose it.

Caramel-Stuffed Chocolate Chip Cookie Cups

Prep Time: 20 minutes | Cook Time: 13 minutes | Total Time: 33 minutes | Servings: 12 cookie cups

Ingredients

  • 1 cup (2 sticks) unsalted butter, softened
  • 3/4 cup granulated sugar
  • 3/4 cup packed light brown sugar
  • 2 large eggs
  • 2 teaspoons pure vanilla extract
  • 2 1/4 cups all-purpose flour
  • 1 teaspoon baking soda
  • 1 teaspoon fine salt
  • 2 cups semi-sweet chocolate chips
  • 12 soft caramel candies (such as Kraft caramels), unwrapped
  • Flaky sea salt, for finishing (optional)

Instructions

  1. Preheat and prep. Preheat your oven to 350°F. Grease a standard 12-cup muffin tin generously with butter or non-stick spray, making sure to coat the sides.
  2. Cream butter and sugars. In a large bowl, beat the softened butter, granulated sugar, and brown sugar together with a hand mixer or stand mixer on medium speed until light and fluffy, about 3 minutes.
  3. Add eggs and vanilla. Beat in the eggs one at a time, then add the vanilla extract and mix until fully incorporated.
  4. Add dry ingredients. Reduce mixer speed to low. Add the flour, baking soda, and salt, mixing until just combined — do not overmix.
  5. Fold in chocolate chips. Stir in the chocolate chips by hand with a rubber spatula until evenly distributed throughout the dough.
  6. Build the cups. Scoop about 2 tablespoons of dough into each muffin cup and press it down to form a base. Place one unwrapped caramel candy in the center of each. Top with another heaping tablespoon of dough, pressing the edges down gently around the caramel to seal it in.
  7. Bake. Bake for 11–13 minutes, until the edges are golden brown and set but the centers still look slightly underdone. Do not overbake — the caramel continues cooking after the pan comes out of the oven.
  8. Cool in pan. Let the cookie cups cool in the muffin tin for at least 10 minutes before attempting to remove them. Run a thin knife around the edge of each cup to release. Finish with a pinch of flaky sea salt if desired.

Nutrition (per serving)

Calories: 385 | Protein: 4g | Fat: 19g | Carbs: 51g | Fiber: 1g | Sodium: 290mg

Bobby Tran
About the cook who shared this
Bobby Tran
Week 497 of Bobby’s 30-year story · Houston, Texas
Bobby Tran was born in a refugee camp in Arkansas to parents who fled Saigon with nothing. He grew up in Houston straddling two worlds — Vietnamese at home, Texan everywhere else — and learned to cook from his mother's pho and a neighbor's BBQ smoker. He's a former shrimper, a recovering alcoholic, a divorced dad of three, and the guy who marinates brisket in fish sauce and lemongrass because he doesn't believe in borders, especially when it comes to flavor.

How Would You Spin It?

Put your own twist on this recipe — what would you add, remove, or swap?