Preheat oven to 400°F. Line a cookie sheet with parchment paper or foil. Remove the pits from the dates if needed. Slice the dates lengthwise to remove the pit.
In a small bowl, combine goat cheese and jalapeno. Stuff each date with the goat cheese mixture. Close the date as much as possible to prevent the cheese from melting out.
Wrap each date tightly with half a bacon, seam side down, or secure with a toothpick.
Combine maple syrup, pepper, and cayenne in a small bowl. Brush mixture over each wrapped date.
Bake approximately 30 minutes or until the bacon is crispy. Place on a paper towel-lined plate to remove any excess grease (if desired). Let cool for a couple of minutes. Serve.
Store leftovers in an airtight container in the refrigerator for 4-5 days.