Drunken Chocolate-Cherry Hamantaschen for Purim

Naomi Ross | JNS

As a kid in my mother’s house, I’d use a drinking glass to cut out my rounds of dough for hamantaschen, those triangular Jewish cookies made for the holiday of Purim. Dipping the rim in flour, it was a careful practice of cutting as close together as possible, leaving the least amount of scraps behind (the fewer scraps to reroll, the better; the dough tends to get tougher with each redo).

The tradition to give mishloach manot (festive food gifts to neighbors and friends) on Purim spurred my desire for fun after-school projects in the days leading up to the holiday. For a young person, taking ownership of preparing a package to give to others was a momentous experience. It required me to think about someone else and how to make it special for them.

We kept it simple — traditional apricot- or prune-filled. No frills but delicious all the same.

Now, as an adult with my own family, I have fun playing with different versions and more sophisticated flavors. One year, I used guava paste and lime. Each year, my family prepares and gives several packages to friends and neighbors, but lately, I also try to think of someone who in particular needs a lift or smile and make sure they get one, too. That extra attention and loving touch make a difference, especially when cooking for others.

Those pesky, sealed edges of the hamantaschen can reopen when baking, so always pinch twice!

As per the recipe below: No, it’s not alcoholic. Yes, the alcohol cooks out, leaving a lusciously decadent filling. Yes, cherries and chocolate need to be together. And yes, give some to your friends — if there are any left.

The dough can be prepared up to three days in advance. The filling can be made up to a week in advance.

Drunken chocolate-cherry hamantaschen | Dairy or pareve

(From “The Giving Table” by Naomi Ross, November 2022)

Makes about 5 dozen hamantaschen

For the dough:

• ¾ cup oil
• 1 cup sugar
• 3 eggs
• ¼ cup milk or soy or oat milk
• 1½ teaspoons. pure vanilla extract
• 3½ cups flour, plus more for flouring
• ⅔ cup Dutch-process cocoa (pareve)
• 4 teaspoons baking powder
• ¼ teaspoon salt

For the filling:

• 1 (12-ounce) bag frozen dark pitted cherries, thawed
• ⅓ cup dry red kosher wine
• ¼ cup sugar
• 1 tablespoon cornstarch
• ¼ teaspoon cinnamon

Cream the oil and sugar together in an electric mixer until a grainy paste forms. Beat in eggs, milk and vanilla until well-blended.

In a separate large bowl, sift together the flour, cocoa, baking powder, and salt. Slowly add the flour mixture to the batter, a little at a time, mixing at low speed until the dough comes away from the sides of the bowl and forms into a ball. Wrap in plastic wrap and refrigerate for at least two hours or overnight. While the dough chills, prepare the filling.

Combine all filling ingredients in a medium saucepan and stir to blend until all cornstarch is dissolved and no lumps are visible.

Place saucepan over medium heat and bring to a simmer. Cook for 5 to 7 minutes, stirring often until the mixture is thickened and bubbly. Remove from heat to cool; chill to thicken.

Preheat oven to 350 degrees F. Line three baking sheets with parchment paper. Divide dough into four parts. Roll out the dough on a lightly floured board (it helps to flour the rolling pin as well) into a very thin round, about ⅛-¼-inch thick. Using a 3–3½-inch diameter cookie cutter or glass, cut circles in the dough. Place one cherry with a little of the sauce in the center of each circle. Shape into a triangle by folding the three sides inwards toward the center (leaving space for the filling to be open and visible); pinch the sides together tightly.

Place hamantaschen 1 inch apart on prepared baking sheets (pinch again to secure folds). Bake for 12 to 14 minutes. Be careful not to overbake. Repeat with the remaining dough, using up dough scraps as well. Transfer baked hamantaschen to racks to cool. For a pretty look, drizzle with a little melted white chocolate (or dip one-half of the hamantasch into white chocolate).