Preheat your oven to 375°F (190°C). Lightly grease an 8x8 inch baking dish.
In a medium bowl, combine the pineapple chunks with 1 tablespoon of the date sugar. Toss to coat and set aside.
In a large bowl, combine the remaining date sugar, gluten-free flour, and oats. Using a pastry cutter or your fingers, work the cubed butter into the dry ingredients until the mixture resembles coarse crumbs.
Stir in the honey and cinnamon until well combined.
Spread the pineapple mixture evenly in the prepared baking dish. Top with the oat crumble mixture, making sure to cover the pineapple completely.
Bake for 30-35 minutes, or until the topping is golden brown and the filling is bubbly.
Let the crisp cool slightly before serving. Enjoy warm or at room temperature, topped with a scoop of vanilla ice cream or whipped cream (optional).