Blanch the broccolini in a large pot of boiling salted water for 5 minutes. Remove the broccolini from the pot (reserve all of the cooking liquid) and immerse in a bowl of ice water to stop cooking process.
Bring the reserved cooking liquid back to a boil and cook the penne in that water until tender but still firm to the bite (about 10 minutes). Drain the pasta, reserving 1 cup of the cooking liquid.
Meanwhile, in a large skillet, heat the olive oil over medium heat. Add the sausage and cook, breaking it up with spoon, until browned and juices form, about 8 minutes. Add the garlic and red pepper flakes and sauté until fragrant, about 30 seconds. Add the broccolini and toss to coat. Add the penne and enough reserved cooking liquid to moisten. Stir in the Parmesan cheese, salt and pepper to taste.
Open up the wine and enjoy!