Tomato Soup and Grilled Cheese Salad

Tomato Soup and Grilled Cheese Salad

Hey nonny nonny and a ho ho ho, did everyone have a happy holiday?

I’m still over on the east coast, hanging out with my mom, cooking and eating and relaxing, and running at an old park that I totally undervalued when I lived here.

In other news, I realize that I have a genetic compulsion to feed other people. The first words that my grandma would say to me upon arrival on her doorstep were invariable: “did they feed you on the plane?” Why yes, the attendant tucked a napkin into my collar before spooning me some apple sauce.

Tomato Soup and Grilled Cheese Salad

And the first thing that happens when we get to my mom’s house is being showered with cookies (and thankfully beer/wine). Food is love, food is a greeting, food is manners, food is the reason for family gathering.

Jason, on the other hand, grew up in a mild Midwestern home, where the purpose of food was bodily nourishment. Potatoes, sour cream, tinned broccoli and beans.  Food is tidily stored in the cupboard and dilly dip is the prelude to dinner. You don’t spend all day in the kitchen, the opposite of my family’s norms. Cook and clean and then repeat.  Snack were a pastime, and as the kids (i’m one of the kids) got older, wine was added to the mix. When you grow up like this, you eventually train yourself to work around the rolling feast, pass by it without swallowing each crumb. Well, sometimes. My willpower isn’t always as willful as I’d like. And Jason hasn’t had any conditioning to the constant food environment, so when my mom waves muffins and bacon his way, he won’t pass on them.

Tomato Soup and Grilled Cheese Salad

What we both needed was a healthier way around the comfort meals. Like most people, I adore comfort food, but I also wish it was lighter and more nourishing. Luckily, mom mom likes greens as much as she likes cookies, so there was no fuss or objection to this alteration. Tomato soup and grilled cheeses became the addendum to the meal instead of the centerpiece. The flavors are still present, but warmly served atop greens.  Filling, but still room for the Christmas cookies that might be still rolling around.


Yield: 2-4


    for the dressing
  • 3.5 tbsp herby tomato paste
  • 1/2 cup loose packed basil
  • 2 tbsp balsamic vinegar
  • 3 tbsp olive oil
  • 1/2 tsp minced shallot
  • 1 cup grape tomatoes
  • 1/2 cup grapefruit juice
  • 1/4 cup water
  • salt and pepper to taste
  • for the salad
  • 3 big handfuls of dark greens (I used kale, then wilted it)
  • 2 oz peppered goat cheese
  • 1 red bell pepper
  • one small handful each of:
  • arugula
  • watercress greens
  • grape tomatoes
  • blackberries
  • parsley
  • toasted pecans
  • for the sandwiches
  • 2 slices gluten free bread
  • sharp cheddar
  • olive oil or butter


    for the dressing
  1. Combine all ingredients in a blender until smooth. Dressing will be thick and creamy. A small pour imparts a great deal of flavor, which means you can avoid the soggy, overdressed vinegary salad.
  2. for the salad
  3. Toss all ingredients in a bowl until combined
  4. for the sandwiches
  5. I find that gluten-free bread is often firm and hearty. It's easy to slice in half to form two thinner slices (aka slice along the crust). The thinner slices soak of cheese better and get toastier faster. They taste like cheese straws when cooked this way. Skillet -toast the sandwiches until gooey and brown, then cut into triangles and place over the salad like big croutons. One or two sandwiches is plenty.


4 side portions, or 2 main portions

Tomato Soup and Grilled Cheese Salad

P.S. the title of this post reminds me of this




6 thoughts on “Tomato Soup and Grilled Cheese Salad

  1. Salad looks amazing, full of colorful healthy and delicious ingredients! I never thought of putting grilled cheese on a salad, what a great idea!

    1. Haha I felt the same way when I was writing the title, but I didn’t know what else to call it! “Stuff on top of other stuff in bowl” probably wasn’t going to pass the SEO test. Thanks, lady!

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