Preheat the oven to 400°F.
Chop off the top of the garlic head and drizzle 1 tbsp olive oil on the top. Wrap in foil and bake in the oven for 35 minutes. Let cool and squeeze out garlic cloves and mash it. Set aside.
Bring a large pot of salted water to a boil and cook pasta according to pasta instructions.
In a large skillet over medium heat, heat up the remaining 1 tbsp of olive oil. Add the onion and cook until translucent. Then add in the tomato, red pepper flakes, and herbs, and cook for about a minute. Add in the wine (optional) and cook for another 1-2 minutes, until most of the liquid has evaporated.
Add in the marinara sauce, heavy cream and the baked garlic mash, and bring it to a boil. Season with salt & pepper. Turn off the heat and add in the cooked pasta and parmesan. Mix to combine.
Garnish with parsley and more parmesan and serve!