Preheat oven to 425 degrees. Line a baking sheet with parchment paper.

Slice dates in half without separating halves completely and remove pit. Press 1/4 oz. cheese into the center of the date. Close date and wrap tightly with a half slice of bacon.

Roll in brown sugar. Place on the prepared baking sheet with bacon seam-side down and secure with a toothpick if desired. Repeat with remaining dates.

Bake in preheated oven for 10 minutes, until bacon is crisped all around. Cool slightly and drizzle with balsamic.