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Cookies and Cream Cupcakes -- For the Kid Who Deserves Something Homemade

Tommy turned three. October. A birthday party in the backyard with both families and approximately seven thousand balloons that Megan bought because she is constitutionally incapable of buying a reasonable number of balloons. Tommy ate cake with his hands and pierogi with his hands and everything with his hands because utensils are suggestions when you're three.

He's talking in full sentences now. "Dada make peee-oh-gee." "Mama read book." "Grandpa hold me." "Ellie is loud." All accurate observations. He is a reporter of his own life. He narrates everything. He got this from Megan, who narrates the world to her students all day. The narration gene is strong.

Ellie is six months and she's sitting up and she's eating solid food and she watches Tommy with the same calm focus that Babcia had — the focus of someone who is absorbing everything and processing it silently and will emerge, eventually, knowing more than anyone expected. She ate a piece of pierogi this week. Her first pierogi. She ate it and looked at me and opened her mouth for more. She likes pierogi. Both kids like pierogi. The chain holds across both branches.

Made a chocolate cake from scratch for Tommy's birthday. Three layers. Ganache frosting. Better than the box mix cakes of birthdays past. Megan looked at it and said, "You've been practicing." I have. I've been practicing cakes because my kids deserve homemade cakes and because there is nothing I won't learn to make for the people I love.

The small Polish-American heritage is the small kitchen-identity. The small pierogi-recipe-cards from Babcia Helen (Jake’s grandmother who passed in 2018, who had lived two blocks from the small Bay-View family-house) is the small monthly-Saturday-tradition. The small kielbasa-and-sauerkraut. The small bigos. The small recipes that came over from the small Krakow-region in the small 1910s.

The small Milwaukee-winter is the small six-month-condition. The small cold-weather-comfort-food rotation runs October through April. The small soups, the small stews, the small braises, the small heavy-baked-goods. The small Midwestern-comfort-vocabulary is the small kitchen-language.

Megan and Jake married in June 2024. The small newlywed-rhythm is in its small second year. The small two-bedroom rental on the small east-side of Milwaukee continues to be the small first-home. The small thirty-year-mortgage-eventually-someday is the small five-year-goal. The small marriage is the small foundation the small life is being built on.

Megan and Jake married in June 2024. The small newlywed-rhythm is in its small second year. The small two-bedroom rental on the small east-side of Milwaukee continues to be the small first-home. The small thirty-year-mortgage-eventually-someday is the small five-year-goal. The small marriage is the small foundation the small life is being built on.

The small Lakefront Brewery shift-work continues to be the small steady-paycheck. The small forty-hour-week brewery-floor job pays the small twenty-two-an-hour rate that the small Milwaukee-blue-collar-economy supports. The small benefits are the small union-decent. The small ten-year-tenure-target is the small career-anchor.

The small Polish-American heritage is the small kitchen-identity. The small pierogi-recipe-cards from Babcia Helen (Jake’s grandmother who passed in 2018, who had lived two blocks from the small Bay-View family-house) is the small monthly-Saturday-tradition. The small kielbasa-and-sauerkraut. The small bigos. The small recipes that came over from the small Krakow-region in the small 1910s.

Megan is from a small Irish-Catholic Milwaukee-suburban family. The small Sunday-dinners at her small parents’ house rotate with the small Sunday-dinners at Jake’s parents’ house. The small in-laws on both sides have been the small welcoming-presence. The small two-family-network is the small extended-support the small newlywed-life rests on.

The small Milwaukee-winter is the small six-month-condition. The small cold-weather-comfort-food rotation runs October through April. The small soups, the small stews, the small braises, the small heavy-baked-goods. The small Midwestern-comfort-vocabulary is the small kitchen-language.

The small future-kid-conversations have begun. Megan teaches small fourth-grade at a small public school in Wauwatosa. The small adoption-vs-biological conversation is in the small early-discussion stage. The small five-year-plan includes the small kid-or-kids in some form. The small kitchen is the small place where the small future is being practiced.

The three-layer ganache cake I made for Tommy’s birthday was a milestone for me as much as it was for him — proof that I’ve been putting in the work, that practice in a small kitchen actually compounds into something real. These Cookies and Cream Cupcakes live in that same spirit: chocolate, from scratch, unapologetically celebratory. They’re everything Tommy would have eaten with both hands at that backyard party, and they’re the kind of thing I want to keep learning to make — because there is nothing I won’t learn for the people I love.

Cookies and Cream Cupcakes

Prep Time: 25 min | Cook Time: 20 min | Total Time: 1 hr (includes cooling) | Servings: 18 cupcakes

Ingredients

  • 1 cup all-purpose flour
  • 1/2 cup unsweetened cocoa powder
  • 1 tsp baking soda
  • 1/2 tsp baking powder
  • 1/2 tsp salt
  • 1 cup granulated sugar
  • 1/2 cup (1 stick) unsalted butter, softened
  • 2 large eggs, room temperature
  • 1 tsp vanilla extract
  • 3/4 cup buttermilk
  • 1/2 cup hot water or hot brewed coffee
  • 12 Oreo cookies, roughly crushed (for batter)
  • Cookies and Cream Frosting:
  • 1 cup (2 sticks) unsalted butter, softened
  • 3 cups powdered sugar, sifted
  • 3 tbsp heavy cream
  • 1 tsp vanilla extract
  • Pinch of salt
  • 10 Oreo cookies, finely crushed (for frosting)
  • 6 Oreo cookies, halved (for garnish)

Instructions

  1. Preheat oven. Heat oven to 350°F. Line two standard muffin tins with 18 cupcake liners.
  2. Mix dry ingredients. In a medium bowl, whisk together flour, cocoa powder, baking soda, baking powder, and salt. Set aside.
  3. Cream butter and sugar. In a large bowl, beat softened butter and granulated sugar with a hand mixer on medium-high speed until light and fluffy, about 3 minutes.
  4. Add eggs and vanilla. Beat in eggs one at a time, scraping down the bowl between additions. Mix in vanilla extract.
  5. Alternate wet and dry. On low speed, add the dry ingredients in three additions, alternating with the buttermilk (beginning and ending with dry). Mix until just combined — do not overmix.
  6. Add hot liquid. Stir in the hot water or coffee until the batter is smooth and thin. Fold in the roughly crushed Oreos.
  7. Fill and bake. Divide batter evenly among liners, filling each about 2/3 full. Bake 18–20 minutes, until a toothpick inserted in the center comes out with just a few moist crumbs. Do not overbake.
  8. Cool completely. Let cupcakes cool in the pan for 5 minutes, then transfer to a wire rack. Cool completely before frosting, at least 30 minutes.
  9. Make frosting. Beat softened butter on medium-high speed until pale and creamy, about 4 minutes. Add powdered sugar one cup at a time on low speed. Add heavy cream, vanilla, and salt; beat on medium-high for 2 minutes until fluffy. Fold in finely crushed Oreos by hand.
  10. Frost and garnish. Pipe or spread frosting generously onto cooled cupcakes. Press a halved Oreo cookie into the top of each. Serve immediately or store covered at room temperature up to 2 days.

Nutrition (per serving)

Calories: 340 | Protein: 3g | Fat: 18g | Carbs: 46g | Fiber: 1g | Sodium: 290mg

Jake Kowalski
About the cook who shared this
Jake Kowalski
Week 602 of Jake’s 30-year story · Milwaukee, Wisconsin
Jake is a twenty-nine-year-old brewery worker, newlywed, and proud Polish-American from Milwaukee's Bay View neighborhood. He didn't start cooking until his grandmother Babcia Helen passed away and left behind a stack of grease-stained recipe cards. Now he makes pierogi from scratch, smokes meats on a balcony smoker his landlord pretends not to notice, and writes for guys who want to cook good food but don't know a roux from a rub.

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