Roast your garlic heads. Preheat your oven to 400 F. Chop the top off your garlic heads, just enough so you’re exposing all the cloves. Put the heads of garlic on a piece of tinfoil, drizzle with the 2 tbsp olive oil (about 1/2 tbsp per head), sprinkle each with salt, then close up your tin foil to create a sealed pouch and roast in the oven for 45 minutes. Remove from oven, squeeze out the roasted garlic and mash into a paste. Set aside.

Make your soup. Add 1 tbsp oil to saucepan over medium heat. When then oil shimmers, add your onion and cook till translucent. Add your garlic and cook until fragrant, another minute. Add your can of San Marzano tomatoes, sugar, and salt + pepper. Simmer for 30 minutes, then blend using an immersion blender (or standard blender). Once smooth, add your cream and taste for seasoning again.

While your tomato soup is simmering, make the tomato butter. Mash your room temp butter with tomato paste until combined and smooth. Season with salt and set aside.

Prep your grilled cheeses. Schmear one side of each slice of bread with 1/2 tbsp of tomato butter, then schmear the other side of one slice with roasted garlic and sprinkle on one clove of raw, minced garlic. If you have extra, go crazy and schmear both slices. Have your cheeses ready and waiting.

Cook your grilled cheese. Add 1/2 tbsp butter to skillet over medium heat, then add one slice of bread, tomato butter side down, to the pan. Top with two slices of American cheese, your shredded gruyere, and the other slice of bread, tomato butter side face up. Flip when golden brown and the tomato has caramelized a bit (yum).

Serve your grilled cheeses with tomato soup and enjoy! I like to garnish my soup with an extra drizzle of olive oil and some fresh oregano (optional). So good.