Everything tastes better with bacon. Dates are no exception. When it comes to this salty and sweet finger food, you want to buy the biggest, most plump dates you can find. If this requires pitting them yourselves, I’d recommend doing it. Pit these by making a small slit in the date with a small paring knife and pushing the pit out with a skewer.
I filled my dates with ricotta. To me, it seemed to compliment the sweet dates the best. I have also seen recipes with cream cheese, blue cheese, and Parmesan. The choice is yours. I do recommend keeping the filling very simple. The bacon and the dates really speak for themselves.
No matter what filling you choose, you should keep one thing in mind: thin bacon works best for these dates. Thin slices of bacon will crisp up nicer and easier than thick-cut bacon and as we all know, crispy bacon is like crispy pieces of heaven.
Place the ricotta in the bottom corner of a ziplock bag and seal tightly. Use the scissors to cut the corner of the bag to create a piping bag. Remember, you can always cut more off if necessary, so start smaller. Use the piping bag to fill the dates with the cheese.
Wrap the stuffed dates with a slice of bacon and secure with a toothpick through the belly of the date. Arrange all the prepared dates on a parchment or aluminum foil-lined baking sheet, allowing at least a little space between each one for good browning. Bake for 10 or 15 minutes, until the bacon is browned and crispy, turning the baking sheet around 180 degrees halfway through baking. Remove from the baking sheet and serve.