Start by washing the acorn squash and patting them dry. The skin of acorn squash is edible, so there's no need to peel it. Cut the small squash in half vertically and scoop out the seeds and any stringy pulp using a spoon.
Mix the olive oil, brown sugar, and a pinch of salt in a small bowl. This savory-sweet blend will enhance the flavor of your acorn squash.
Brush the flesh of the squash halves with the seasoning mixture. Make sure to coat them evenly for the best flavor.
Preheat your air fryer to 350 degrees. (The cooking time may vary depending on the size of your air fryer and the type of air fryer you have, so double-check your user manual for specific instructions.)
Line the air fryer basket with liners or parchment paper. You can lightly grease it with cooking spray if you want. This will prevent the squash from sticking to the basket; I did not.
Place both halves of the seasoned acorn squash in the air fryer basket, cut side up.
Cook the squash at 350 degrees for 20 minutes or until they are fork tender and have turned golden brown on the edges.
Brush another layer of sauce mixture over the squash again. Put them back into the air fryer for another 5 minutes for a delightful touch of sweetness.
Once the squash is done, throw in a couple of dried red dates in the squash for another 1 minute or just garnish with fresh herbs. Transfer the air fried acorn squash to a serving platter and enjoy your delicious side dish!