Dessert First

I don’t like sticky-sweet desserts, so my whoopie pies are somewhat less sweet than others. I also don’t like gritty mixtures of shortening and confectioner’s sugar, as is typical in whoopie pie fillings (and American cake frostings), so I combined an old-fashioned cream filling with a bit of marshmallow creme. I know some people want to avoid marshmallow creme, so you could leave it out here and just have a cream filling, in which case you may want to add a touch of vanilla to it. I’ve tried making this with a Swiss meringue to avoid the marshmallow creme but find it doesn’t hold as well as I’d like.

Makes about 4 dozen (can be halved)

Cakes:

• 4 cups all-purpose flour
• 3/4 cup unsweetened cocoa
• 1 teaspoon baking soda
• 1/2 teaspoon fine sea salt
• 14 tablespoons (1 3/4 sticks) unsalted butter, softened
• 1 cup granulated sugar
• 3/4 cup firmly packed light brown sugar
• 1 tablespoon instant espresso powder (optional, but wonderful)
• 2 large eggs
• 1 tablespoon vanilla extract
• 1 1/2 cups whole milk, light cream, or half-and-half
• 1/4 cup Kahlua

Filling

• 1/4 cup all-purpose flour
• 3/4 cup milk
• 3/4 cup (1 1/2 sticks) unsalted buter, softened
• 3/4 cup granulated sugar
• pinch of salt
• 1 tablespoon Sambuca, or a bit more to taste
• 1 cup marshmallow creme (or fluff)

1. Preheat oven to 350 degrees and line baking sheets with parchment paper, or lightly grease sheets.
2. In a medium bowl, thoroughly whisk together the flour, cocoa, baking soda and salt. In a large bowl, beat butter, granulated sugar, brown sugar and espresso powder until well combined. Beat in eggs, one at a time, and vanilla.  Scrape the sides and bottom of the bowl with a spatula and beat again until smooth. On low speed, alternately beat in flour mixture and milk and Kahlua, beginning and ending with flour mixture, just until combined. Scrape bowl with spatula to be sure all ingredients are combined well.
3. Drop batter by tablespoons onto prepared sheets, spacing 1 inch apart.  With moistened fingers, gently press on the dough balls to flatten slightly. Bake for 10 to 12 minutes, until cakes spring back when tops are lightly pressed with a finger; be careful not to overbake. Cool completely on a wire rack.
4. To make filling: In a small pan, thoroughly whisk together flour and milk until smooth. Bring almost to a boil over medium heat, whisking, until very thick. Remove from heat and let cool. In a mixing bowl, beat butter, sugar and salt until smooth and fluffy. Beat in cooled flour mixture, then Sambuca, then marshmallow creme.
5. Spread filling over the flat bottom of half the cakes and top with another cake, flat side facing the filling. Serve, or store in an airtight container. To freeze, wrap in plastic wrap first — taken out in the morning, they’ll thaw perfectly in a lunchbox.