01 - Preheat oven to 400°F (200°C). Toss cubed butternut squash with 1 tablespoon olive oil, 1/4 teaspoon salt, and a pinch of pepper. Spread evenly on a baking sheet and roast for 20 to 25 minutes until golden brown and tender.
02 - In a large skillet or saucepan, heat remaining 1 tablespoon olive oil and 2 tablespoons butter over medium heat. Add onion and cook for 3 to 4 minutes until softened. Stir in garlic and chopped sage, cooking for an additional minute until fragrant.
03 - Add orzo to the pan and stir to coat with fat. Toast for 1 to 2 minutes until lightly colored.
04 - Pour in dry white wine, if using, and stir constantly until it is mostly evaporated.
05 - Add vegetable broth in 2 to 3 increments, stirring frequently and allowing the liquid to absorb before each addition. Continue cooking for 10 to 12 minutes until orzo is tender but remains al dente.
06 - Fold in roasted butternut squash, Parmesan cheese, and red pepper flakes if desired. Adjust seasoning with salt and pepper. Add additional broth or water for creaminess if needed.
07 - Dish immediately, garnished with extra sage leaves and Parmesan cheese.