Add the olive oil to a large skillet over medium heat. Stir in the butternut squash and shallot. Season with salt and pepper. Cook until the shallot is fragrant and the butternut squash is fork-tender, about 8-10 minutes. Stir in the sage and garlic, cooking for an additional 1-2 minutes until fragrant.

Reduce the heat to medium-low and stir in the orzo. Toast the orzo for 1-2 minutes, stirring constantly, until nutty and fragrant. Slowly pour in the white wine while scraping the bottom of the skillet with a wooden spoon. Let simmer until the wine is almost completely cooked off, about 1-2 minutes.

Add 1 cup of the vegetable broth/stock to the skillet, stirring frequently until the orzo absorbs all of the liquid. Continue adding stock/broth ½ cup at a time and stirring frequently until the orzo is creamy and al dente. The butternut squash should break down slightly, creating a creamy sauce.

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

Portion the butternut orzo into individual bowls. Serve immediately, optionally topped with additional grated parmesan or browned butter and crispy fried sage leaves.