Preheat your oven to 400 degrees. In a glass baking dish, toss the squash with the olive oil and fresh cracked black pepper. Spread the squash in a single layer and roast until slightly browned. Roughly 25 minutes. When done, set aside.
In a large sauté pan, cook the pancetta on medium heat, stirring occasionally, until crispy, about 2 minutes. Remove from pan and place on to a paper towel lined plate to soak oil.
Add the shallots and cook until translucent ~ 4 minutes. Then, add the kale and 2 Tablespoons of water. Stir a few times and ensure the kale is evenly wilted and water evaporated. Remove and set aside in a small bowl.
In the same pan, on medium heat, melt butter and saute garlic with 1/2 teaspoon salt and 1/2 teaspoon fresh cracked pepper. Cook for 1-2 minutes until starting to brown, then add wine and fresh sage leaves and cook for another 5 minutes to reduce the liquid. Once reduced, add back kale and pancetta. Keep on low heat until pasta is ready.
Cook the pasta in salted water until al dente and drain once complete.
Transfer the cooked pasta, either in two batches or if your pan is big enough or all at once. Mix in the pasta with the sauce to ensure the pasta is evenly coated.
Stir squash and add the cream. Fold gently and heat on medium until heated through.
Garnish with the fried sage and pine nuts and serve!
Optional: receive hugs from those who get to enjoy this dish with you! (show recipe to those you cooked for 😉 )
Fried sage leaves
To fry the sage leaves, in a small fry pan over medium heat, warm the olive oil until shimmering. Carefully drop the sage leaves, a few at a time, into the oil. They will sizzle and crisp very quickly, in 15 to 30 seconds. Using a fork or small skimmer, transfer the fried sage leaves to a paper towel–lined plate.
If you are not using fresh pasta, you may want to cook your pasta as the first step. Fresh pasta cooks very quickly (~50-60 seconds), thus I moved it toward the end.