Pre-heat oven to 375°F. Line a baking sheet with foil and set aside.
Prepare 2 acorn squash. Cut the stems off the top and the bottom of each acorn squash to create a flat base, making sure not to cut too deep into the base of the squash. Then, slice each squash in half and scoop out the seeds.
Rub the flesh side of the squash with 1 tsp olive oil, then season with salt and pepper to taste. Place the squash halves on the lined baking sheet, large cut side down. Roast at 375°F for 30 minutes. While the squash roasts, toast the pine nuts and prepare the sage brown butter.
Toast pine nuts. Add 1/4 cup pine nuts to a small skillet over medium heat. Heat them until they begin to toast, stirring or flipping continuously to avoid burning. Once most of the nuts are golden brown, remove to a plate to cool. Set aside.
Make sage brown butter. Add 3 tbsp unsalted butter to a small, light colored skillet or pan over medium heat. Once chunks of butter have melted and butter begins to sizzle, add 6-8 fresh sage leaves. Swirl the pan constantly until the butter turns dark golden brown and has nutty aroma, about 4-6 minutes. Remove from heat, and pour into a bowl or jar, then remove the sage leaves to a paper towel lined plate. Set aside.
Flip the squash and broil. Once the squash has roasted at 375°F for 30 minutes, flip the squash so that the bowl of the squash is facing up. Set oven to broil and broil the squash for about 5 minutes to brown the edges, watching closely to remove them before they burn.
Remove the squash to a serving platter and immediately sprinkle with 2 tbsp light brown sugar. Drizzle the squash halves with the brown butter and crumble the fried sage over top. Sprinkle with pine nuts and flakey sea salt before serving.