Preheat oven to 350 degrees Fahrenheit or 175 degrees Celsius.
Line a baking sheet with parchment paper or aluminum foil and add the pecans. Bake for 8-10 minutes, until fragrant and toasted.
Let cool, then chop into small pieces.
Meanwhile, pour balsamic vinegar into a small saucepan and bring to a simmer over medium-high heat. Simmer for 8-10 minutes, until vinegar has reduced and thickened. You should have about 3 tablespoons left. Let cool until ready to use.
Peel off any bruised leaves on your endive, then rinse.
Cut off bottom of each endive, then peel each leaf off and place on a paper towel to dry. As you make your way peeling leaves from the outside to the inside, you may want to cut off the bottom of the endive as you go so that the leaves continue to come off easily.
Prepare your dates by chopping into small pieces.
Crumble your blue cheese into small chunks.
Now it’s time to assemble. Lay your endive cups onto your serving platter and sprinkle a little of each of the main ingredients: chopped pecans, chopped dates, and crumbled blue cheese. No need to measure anything, just eyeball that you have roughly the same amount of each.
Drizzle with balsamic vinegar reduction and serve.
Notes
You can prep your ingredients in advance with the exception of the endive cups, which will wilt and turn brown at the edges. Note that if you make the balsamic syrup in advance, it will thicken as it cools. If it is completely cold and too thick when you are ready to use it, just microwave it for a few seconds to warm it up a bit.