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.
Pasta
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.