On a baking sheet, toss together the olive oil, butternut squash, shallot, garlic, oregano, and a pinch each of chili flakes, salt, and pepper. Bake 20-25 minutes, until the squash is tender.
Pop the garlic cloves out of their skin. Add the butternut squash, shallot, garlic, and ricotta to a food processor. Puree until smooth. Season with salt and pepper.
In a large, oven-safe skillet with sides, bring 3 1/2 cups water to a boil, add the pasta, and cook, stirring often, until the pasta is al dente, 8 minutes. Stir in the pureed butternut squash. Add the milk/ cream, Italian seasoning, spinach, and sun-dried tomatoes, stirring to combine. Stir in the gouda and parmesan until melted.
Remove from the heat and top with the provolone cheese. Bake 15-20 minutes, until the cheese is melted and gooey. Eat!