1. Preheat oven to 425ºF and line a baking sheet with parchment paper.
2. Slice date in half without separating halves completely and remove pit. Press 1/4 ounce of cheese into the center of 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.**
3. Bake in preheated oven for 10 minutes, and then flip dates, carefully pressing any loose melted cheese back into the dates as best as possible. Bake another 10-12 minutes, until bacon is crisped all around. Cool slightly and serve with balsamic reduction.

Balsamic Reduction

1. In a small saucepan, bring balsamic vinegar to a low boil over medium heat. Reduce heat to maintain a simmer and simmer until the vinegar has reduced to about 1/4-1/2 of the original amount, or until as thick as desired (Reduce more for drizzling and less for dipping). For me, this took about 25 minutes, although times will vary based on stove differences.
2. Allow to cool briefly before serving. Serve balsamic reduction in a bowl for dipping or drizzle on dates just before serving. A spoon or a pastry bag fitted with a small round tip can be used for drizzling.