School’s Out Chocolate Cupcakes with Whippy Chocolate Frosting

It’s Sunday, so that means Alyssa is sad. There’s always something sad on a Sunday for that child of mine. This week, it wasn’t that she had to wear a dress, but because the big sister would share her bubbles, her ball, her spot on the couch. There were many, many things to be sad about today, but the more horrid of all trickled into her mind well past bedtime. It was nearly ten o’clock when I went into her room for a late night tuck and discovered her weeping.

“Baby, what is wrong?” I begged of her, cradling her tender cheeks with my lips as I spoke.

“I don’t want to go to school anymore! I just want it to be summer!” Whimper. Gasp. Sniff.

It didn’t matter that there are two field trips this week. It didn’t matter that she’s a mere six days from the bliss of summer freedom. All she knew was that she was home and safe and wearing pajamas, and all of that would change at 6 a.m. tomorrow when her alarm clock rings.

I was tempted to tell her she’d be just fine and the week was going to fly by, but remembered the words of Gretchen Rubin in The Happiness Project when she says that acknowledging a person’s feelings can actually help them get over them.

So, rather than saying, “girlfriend, it’s late. You’re tired.” I ran my fingers through her hair and said, “Lyss. I can tell you are so sad to think about going back to school tomorrow.”

“I ammmmmmm!” she wailed.

I’m so sorry, I said.

Then her daddy came and kissed her and offered a tuck and she was asleep before one could say overdramatically exhausted.

But you see, here’s the secret. I feel just the same as that little Alyssa of mine. Bring on the sunshine. Call off the routine. I’m ready for lazy days and lollipops. I want to walk barefoot through the green grass of our backyard and read books at absurd hours of the afternoon. Why do we have to go to school anyway?

Well, thank goodness. In six days, we don’t.

So to celebrate, here is one of my favorite ways to treat a class full of students to an end-of-summer treat. These chocolate cupcakes are sure to win you the title of Room Mother Extraordinaire. Popping  a wee, colorful sucker right inside makes a quick and simple decoration that kids of all ages are sure to adore.

Kids and moms. Cupcakes and the Last Day of School. It’s the simple things, you know.


Whippy Chocolate Frosting


2 sticks butter
1 ½ c. brown sugar
3 eggs
2 squares unsweetened baking chocolate
1/2 Tbsp. olive oil
1 c. milk
½ tsp. baking powder
½ c. cocoa powder
1 c. flour
1 tsp. pure vanilla

1 (8 ounce) package cream cheese, softened
1/2 cup white sugar
1/3 cup cocoa powder
1 teaspoon vanilla extract
2 cups heavy cream


In a large bowl, cream butter, sugar and eggs until extremely fluffy (this step is CRUCIAL. Don’t skip it!). In a small bowl, microwave baking chocolate and olive oil just until melted (about 1 minute), stir, add to batter. Add remaining ingredients and whip until evenly incorporated but DO NOT MIX. Fill cupcake wrappers 2/3 full with batter, then bake in an oven preheated to 350 degrees for 18-20 minutes.

In an electric mixer fitted with the whisk attachment, beat together the cream cheese, sugar, cocoa powder and vanilla. While the mixture is still whipping, slowly pour in the heavy cream. While whipping, turn off your mixer and scrape the bottom of the bowl. Beat until the frosting holds a stiff peak.

Pipe frosting from a pastry bag fitted with a large star tip onto cooled cupcakes.