Preheat your oven to 400°F (200°C). Spread the cubed butternut squash onto a baking pan lined with parchment paper, and drizzle with 2 tablespoons of olive oil. Roast the squash for about 25 minutes, or until it's golden and easily pierced with a fork. I find roasting brings out a delicious sweetness in the squash.
While the squash roasts, bring a pot of salted water to a boil. Add the gnocchi and cook according to the package instructions, usually until the gnocchi float to the surface, about 2-3 minutes. Drain and set aside.
In a large skillet over medium heat, add 2 tablespoons of olive oil. Sauté the diced shallot with 1 tablespoon of minced garlic for about 5 minutes until the shallot is translucent. Then add the thyme and chopped sage, and cook for an additional 2-3 minutes until fragrant.
Transfer the sautéed shallot, garlic, herbs, and the roasted butternut squash from Step 1 to a blender. Pour in 1 1/2 cups of milk, add 1/2 teaspoon red pepper flakes, and 1/2 teaspoon salt. Blend everything until you have a completely smooth sauce, adding more milk if you'd like a thinner consistency. I like to taste the sauce for salt at this point and add a touch more if needed.
Pour the blended sauce into a pot over medium-low heat. Stir in the grated parmesan cheese until fully melted and incorporated into the sauce.
In the same pan used for the aromatics, heat 1 tablespoon of olive oil over medium heat. Add the kale and the final tablespoon of minced garlic, and sauté until the kale wilts and turns a vibrant green, about 3-5 minutes. For a pop of color and nutrition, don’t skip this step!
Add the cooked gnocchi from Step 2 and sautéed kale from Step 6 into the pot with the sauce from Step 5. Gently fold everything together to ensure the gnocchi are coated and the kale is evenly distributed. Heat through for 2–3 minutes. I like to let the dish sit off the heat for a minute before serving to let the flavors meld.
Spoon the creamy butternut squash gnocchi into bowls and top generously with extra grated parmesan cheese. Enjoy while hot!