Tomato Soup and Grilled Cheese Sandwiches for Grown-ups

by | Nov 12, 2019

I love making Friday night feel like the weekend has really started. In fact, if I do it really well, it almost feels like a 3-day weekend.

I guess it’s sort of a throw back to school days. Monday through Thursday was always after-school homework and chores, but Friday? Ahhh, Friday … homework could be put off until Saturday. Or Sunday. Or Sunday night. Fridays were for pajama parties and comfort food.

With just that in mind and with family coming for dinner, I made the ultimate in Friday night comfort food – grilled cheese sandwiches and tomato soup. Except I elevated the crap out of it.

Where I grew up in Texas, tomato soup was canned Campbell’s and grilled cheese was Wonder bread with margarine and American singles. This, is not that.

I’ve been making my own tomato soup for years à la Bobby Flay, with a healthy pinch of cayenne pepper and topped with grated Monterey Jack, avocado chunks and tortilla chips.

This version was inspired by a fresh tomato soup I had on my last trip to Paris, finished with a drizzle of basil pesto, which was unforgettable. It takes two minutes to whip up the pesto, and it takes the soup to a whole new level.

Homemade tomato soup is super quick and simple to make, and bears almost no resemblance to the canned stuff.  In fact once you make this, you will probably never buy it in a can again (if you ever did, because it’s really not that good).

And the grilled cheese was, well, let me just give you the recipes.

Homemade Tomato Soup

Serves 4

  • 2 T extra virgin olive oil
  • 2 T unsalted butter
  • 1 onion, roughly chopped
  • 4-6 cloves of garlic, roughly chopped
  • 2 c white wine (I use Sauvignon Blanc)
  • 10 – 12 ripe tomatoes, seeds removed, or 2 28 oz. cans of San Marzano diced tomatoes
  • Salt, if needed, to taste
  • (Optional) ¼ – ½ c heavy cream

Heat the oil and butter in a large pot or Dutch oven over medium low heat. Add the onion and garlic and cook about 4-5 minutes. (This is called “sweating” – softening the vegetables without browning them.)

Add the wine and simmer about 5-10 minutes until the wine is reduced. If you really don’t want to use wine or don’t have a white wine to hand, you could add chicken or vegetable broth. But the wine adds great flavor.

Add the tomatoes and simmer about 20-25 minutes if you’re using fresh, or 10-15 if you’re using canned. I normally use fresh tomatoes, but since it’s November and tomatoes aren’t at their peak, I used canned San Marzano.

Once it’s simmered, let it cool just a few minutes then get after it with an immersion blender until it’s nice and smooth.

Add a little water, if needed, and salt to taste. Stir in a little heavy cream, if you want cream of tomato soup.

Boom – that’s it.

By the way, the trick to an immersion blender is to keep it immersed. You don’t want to lift it up so high that the vents on the side are above the level of the liquid, otherwise you could be wearing your soup.

Pesto sauce

  • ½ cup fresh basil leaves
  • ½ cup extra virgin olive oil
  • 2 cloves garlic
  • ¼ cup pine nuts
  • Parmesan cheese*
  • Pinch of salt

*Pesto normally has parmesan cheese as an ingredient, but since I was serving this with grilled cheese sandwiches, I felt like adding cheese to the pesto was gilding the lily.

Throw a handful of basil leaves in the blender, processor, or NutriBullet, add the olive oil, garlic, pine nuts and salt, and whip it up. Add more oil if it’s too thick. Taste it to see if it needs more salt. Done.

Drizzle on top of the soup.


Elevated Grilled Cheese Sandwich

I used my homemade sourdough bread, but you can use any good, artisanal bread, sliced to your desired thickness.

Coat one side of the bread with mayonnaise, yep, mayonnaise, and place it in a skillet over low heat until crisp and golden. Remove from heat. This is the inside of your sandwich.

Butter the “bare” side of half the bread slices, place them back in the pan, and top with a mixture of melty cheeses. I used Monterey Jack, gouda and parmesan. Butter the other “bare” side of the bread and top off your sandwiches, butter side out.

Cook them low and slow – to give the cheese plenty of time to melt. When it’s beautifully golden on the bottom, flip it over and toast the other side low and slow.



Add a glass of wine, and enjoy your almost 3-day weekend!



  1. Crystal

    Sounds delicious!

  2. Koko

    God sounds awesome!!!!

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