Cook bacon until 2/3 to 3/4 done, then cut strips into thirds. Soak Tooth Picks in Water.
Open the pitted Dates enough to stuff with a small wedge of Pineapple cut from the rings.
Wrap with prepared Bacon and secure with Tooth Picks you have soaked in water. Dip and roll in the Brown sugar. Place on foil lined cookie sheet or pizza platter.
Bake at 350 degrees for 30/40 minutes. Turn pieces half way through cooking to assist in preventing sticking. Brown Sugar and Sugar in Dates is prone to sticking.
When Bacon appears crisp remove from oven and allow to cool for a few minutes. Scrape from foil with spatula if necessary.
These go fast and are a welcomed surprise to guests. My sister is renowned for her Rumaki at our Holiday Gatherings. So, I got a sideways glance when I first arrived with these. All was forgiven when she realized I wasn't a Total Copycat.