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Step 1
Bring a large pot of salted water to a boil. Meanwhile, strip kale leaves from ribs and stems, then tear leaves crosswise into 2"–3" pieces. Cook kale in boiling water until bright green and slightly softened, about 2 minutes. Using tongs, transfer kale to a colander and rinse under cold water, tossing; squeeze out excess liquid from leaves. Keep water at a boil (you’ll use it for the pasta).
Step 2
Whack garlic with the side of a chef’s knife to crush; peel off skins. Heat ¼ cup oil in a large heavy pot over medium. Cook garlic, stirring occasionally, until sizzling, about 3 minutes. Season very generously with black pepper and cook, smashing with a wooden spoon, until cloves break into rough pieces, soften, and look golden. Add kale to pot and cook, stirring often, until darkened in color and very tender, about 8 minutes (garlic will break into even smaller pieces). Season with kosher salt and pepper.
Step 3
Meanwhile, cook pasta, stirring occasionally, until very al dente (2–3 minutes less than package directions).
Step 4
Using tongs, add pasta to kale; splash in about 1 cup pasta cooking liquid. Cook, tossing and adding more pasta cooking liquid as needed, until sauce lightly coats pasta, about 2 minutes.
Step 5
Serve pasta topped with Parmesan, red pepper flakes, sea salt, and more black pepper.