Heat 1/4 cup olive oil in a large, heavy-bottomed skillet over medium-high heat. Once oil is shimmering, add the finely diced onion. Sauté until onion is softened and lightly golden, about 3-5 minutes.
Reduce the heat to medium. To the skillet, add the halved cherry tomatoes, minced garlic, Italian seasoning, optional red pepper flakes, balsamic vinegar, and honey. Season the mixture with 1/2 tsp of salt and 1/4 tsp of pepper (or to taste). Cook until tomatoes begin to soften, about 5–6 minutes, stirring occasionally. As tomatoes soften, smash them with the back of a wooden spoon. Continue cooking for 2–4 more minutes or until the mixture forms a chunky sauce.
In the meantime, fill a large pot with 12 cups of water and bring to a boil. Add 1 tablespoon salt, followed by the pasta. Cook for 1 minute less than the package directions for al dente. Before draining, reserve 1 cup of the pasta cooking water.
Remove the skillet from the heat. Transfer the drained pasta directly from pot into the skillet with the tomato sauce. Gradually add in 1/2 cup reserved pasta water while tossing with tongs until the pasta is well-coated with the sauce. If necessary, add more pasta water. Sprinkle in the ribboned fresh basil. Taste and adjust the seasoning as needed.
Divide among plates. Finish each serving with a drizzle of olive oil and use a microplane to grate fresh Parmesan right on top. Enjoy immediately!
Notes
Note 1: Use only half of a 16-ounce package, which is 8 ounces of pasta. The sauce proportions are designed for this amount. I place a liquid measuring cup on a food scale, zero it out, and add pasta until it reaches 8 ounces. Reserve 1 cup of pasta water, though you may not need it all.Note 2: Cut the basil into thin ribbons, also known as a chiffonade, to help it distribute evenly throughout the dish. Add it just before serving to prevent browning.Storage: Best eaten right away!