Spread a thin layer of cream cheese on one slice of challah and top with two more slices to form a stack. Repeat for the second stack.

Whisk the eggs and milk in a shallow bowl. Dip each stack in the mixture, coating evenly.

Heat 2–3 cups/480–720 ml oil in a deep skillet or small pot to 350°F/175°C. Carefully submerge the stacks and deep-fry until golden brown on all sides, about 2–3 minutes per side.

Transfer to a wire rack for 1–2 minutes to drain excess oil. While still warm, roll or sprinkle with sugar.

Top with whipped cream, grated chocolate, and drizzle with maple syrup. Serve immediately while warm but not hot.