Add olive oil to a large skillet over medium heat. Stir in butternut squash and shallot. Season with kosher salt and ground black pepper. Cook for 8-10 minutes until shallot is fragrant and butternut squash is fork-tender. Stir in sage and garlic; cook for 1-2 minutes longer.

Reduce heat to medium-low and stir in orzo. Toast orzo for 1-2 minutes, stirring constantly. Deglaze skillet by pouring in white wine while scraping browned bits from the bottom. Simmer until wine is almost completely cooked off, about 1-2 minutes.

Add 1 cup of vegetable broth/stock and stir frequently until orzo absorbs the liquid. Add remaining stock/broth ½ cup at a time, stirring frequently. Taste for doneness after 10 minutes; orzo should be creamy and al dente.

Once orzo is al dente, stir in shredded kale, grated parmesan, butter, and nutmeg. Remove from heat once kale is wilted and tender. Taste and adjust seasonings as needed.

Portion into individual bowls, topping with additional grated parmesan or a drizzle of browned butter and crispy fried sage leaves if desired. Serve immediately.