Preheat oven to 350°F (convection). Beat room-temperature butter in a stand mixer or by hand for 3–5 minutes, until pale and off-white.

Add brown sugar and granulated sugar. Beat until light and fluffy, about 2 minutes.

Mix in the egg until combined. Add vanilla extract and molasses (optional).

Add flour, baking soda, baking powder, espresso powder, cocoa powder, and salt. Mix on low speed if using a stand mixer, or gently fold with a spatula until a dough forms.

Scoop 1/3 cup (56 g) of dough and place one ball on a baking tray. Bake this test cookie first to check oven temperature, spread, and flavor before baking the full batch.

Once satisfied with the test cookie, scoop remaining dough and place on the tray. Gently mold into heart shapes and roll in granulated sugar if desired. Use the test cookie to determine spacing. Bake for 9–10 minutes.

Let cookies cool on the tray for 10 minutes, then transfer to cool completely. Chill cookies in the fridge before frosting.

For the frosting, beat butter and shortening together until pale. Add powdered sugar and mix until smooth. Pour in heavy cream and extracts, then whip until light and fluffy. Optional: fold frosting with a spatula to remove air bubbles before piping. Pipe or spread frosting onto chilled cookies. Crumble one cookie and sprinkle on top.