(Fancy) Grilled Cheese and Tomato Soup

It’s cold, it’s gray, your feet are wet, and your hair is a frizzy mess. You’re late for work, you forgot to wear your wellies and you are now stuck walking in wet shoes all day. That’s right, it’s a rainy day. All you want to do is stay inside and curl up in sweatpants. Now, it is my belief that grilled cheese and tomato soup are the culinary equivalent of sweatpants. They swaddle you in comfort, they warm every inch of you, they make going outside and leaving your cocoon of contentment seem like an insurmountable task. Grilled cheese and tomato soup is a classic cruddy day antidote. Now, most people would break out the Wonder bread and Kraft singles, pop open a can of Campbell’s and call it a day. I am not most people. I have a slightly more…refined (read more dishes to wash) approach to this meal. If you have ever met me you know the word “simplicity” is not found often in my vocabulary. I want to do it bigger, better, and more complicated than it has to be. And now I have an excuse…it’s for the blog! I can’t blog about reheating condensed soup now can I? Who’s going to read that? So last night I made a delicious meal of Roasted Butternut Squash and Tomato Soup with two types of  sandwiches; Jarlsberg grilled cheese with caramelized onions and grilled blue cheese with honey.

The inspiration for the soup came from this amazing soup I used to get at the grocery store by Villanova. It was pre-packaged in the refrigerated section and it was to die for. I could eat an entire container (which serves four) in one sitting. It’s really creamy, it’s the kind of soup that sticks to the back of your throat and hits every taste bud in your mouth. It’s spicy without being overwhelming and it’s layered with strong flavors. I’ve tried for the longest time to replicate this delicious soup with little success. It has a very light orangey color, which I thought was a result of adding tons of cream. But the more cream I would add the more pink it would turn, and I never hit the flavor note I was looking for. Well last night I decided to do some research. I was determined to find the ingredients online, I had a basic idea, onions, garlic, basil, tomatoes, cream…but there was something else…something that made this soup more complex than others. Then on a random website, there it was. The ingredient label. I cried out in excitement to my empty apartment and I’m pretty sure I scared the pigeons in the alley. I began to read, garlic, check, onions, check, tomatoes, check, thyme…oh interesting, but not going to make that big of a flavor difference, basil, check, butternut squash…gasp! Yes of course! Butternut squash, that’s how it gets the orangey color, the thick consistency to stand up to all that cream, and that extra punch of flavor. I practically skipped to the grocery store on a food high. Having worked out the soup recipe I moved onto the sandwiches.

I wanted to do a grilled cheese that was a play on French Onion soup, lots of caramelized onions (like those found at the bottom of the soup) and then Gruyere cheese (which gets melted over the top of the soup and bubbles and browns under the broiler.) I had seen it on a blog and wanted to try it out, plus I love caramelizing onions (I realize that statement makes me sound weird, but I find it very relaxing.) So I headed over to the cheese section and searched (in vain) for gruyere cheese. When it was clearly no where to be found I moved on to plan b. and started brainstorming a replacement cheese. I need something that melts well and has a tangy kick that will complement the sweetness of the caramelized onions. I saw Jarlsberg and remembered a scene in The Devil Wears Prada where Vincent Chase (well the actor that plays him) gives Anne Hathaway a grilled cheese, when she refuses it he protests by telling her “hey there’s like $8 worth of Jarlsberg in there.” So I decided if was good enough for Vince it was good enough for me. The other sandwich is an interpretation of this delicious appetizer I once had at a wine tasting. The appetizer was a sliced baguette, brushed with olive oil and toasted, then sprinkled with melted blue cheese and drizzled with honey. The combination of the salty cheese and the sweet honey was perfection, so I thought why not slap these flavors between two pieces of bread and turn it into a sandwich? It would also be great with an apricot marmalade instead of honey or even figs. But we had honey on hand and I wanted to be frugal. I gathered the rest of my groceries including nice crusty bread for the sandwiches and a big beautiful butternut squash. Which, side note was like seven bucks! (Mom, doesn’t that seem a bit high? I mean even for New York!) No matter, I was glad to have found the mystery ingredient in my tomato soup and I skipped home to begin making my comfort meal.

I started with the soup and decided to first tackle the butternut squash. Now there are two ways to cook squash in soup. The first is to peel the squash, cube it, and let the cubes cook and soften in the soup. But I wouldn’t recommend that method because peeling a butternut squash is more difficult than dressing a two year old. The thing just does not want to work with you. It’s oddly shaped, tough to peel, and an all around pain in the ass. Good thing you have me to tell you the easier, better, less stressful way to cook it. Cut the squash in half, scoop out the seeds and roast it for about a half an hour on 450. Roasting it enhances the flavor and brings out the sweetness. The squash will be very soft and can simply be scooped out of the peel using an ice cream scoop. Once I had the squash in the oven the next hour went by in a flash of onions, cheese, and immersion blenders. For the grilled cheese, instead of buttering both sides and frying them, I like to fry them like the French do when they make Croque Monsieurs. I heat olive oil in a deep skillet, add the sandwich and press down with my spatula, melting the cheese, flattening the sandwich and getting a beautiful golden brown crust on the outside.

By the time “Real Housewives of Beverly Hills” was on (thank god Matt has class until 11 and isn’t there to judge my trashy TV watching habits) I was ready to dive in. It was everything I wanted and more. The soup wasn’t an exact match for my grocery store obsession but it was still rich and delicious, so all in all a success. It’s another rainy day today (well it was when I started writing this) and I can’t wait to get home to my leftovers, throw on some sweatpants, cue up the trashy TV, and swim in the comfort of a homemade meal. Here’s how to make it!

Roasted Butternut Squash Tomato Soup


1 lb butternut squash (or use half of a larger one and save the other half for an upcoming recipe.)

2 tablespoons olive oil

1 large onion diced

1 tablespoon of garlic minced

1 table spoon tomato paste

1 teaspoon of basil

½ teaspoon of thyme

1 tablespoon of salt

1 table spoon crushed red pepper

1 28oz can whole peeled tomatoes

1 28oz can crushed tomatoes

1 14oz can chicken broth

1 cup heavy cream


Preheat oven to 450F’

Cut the squash in half lengthwise. Scoop out the seeds and pulp. Brush the cut side with olive oil, place on a sheet pan and roast for 30 minutes until the squash is fork tender. Remove the squash from the oven and scoop out the meat of the squash using an ice cream scoop. Set aside.

In a large pot heat 2 tablespoons of olive oil. Add the onions and garlic and sauté over medium heat until the onion is soft (but not brown.) Add the tomato paste, basil, thyme, salt, and crushed red pepper. Stir to combine. Add the tomatoes and reserved squash. Using a blender or an immersion blender, blend the soup until it reaches a thick puree. When ready to serve ladle into bowls and drizzle a few tablespoons of cream on top.

Jarlsberg Grilled Cheese with Caramelized Onions

Ingredients (makes 4 sandwiches)

Olive Oil

1 large onion sliced thing

6 oz Jarlsberg Cheese

½ loaf of thick crusty bread


In a large skillet heat olive oil, add onions and sauté over medium-low heat, stirring frequently until onions are soft and light brown (approximately 20-30 minutes.) Slice bread about ¾ inch thick, layer slices of Jarlsberg, caramelized onions, and more cheese. Heat additional olive oil in a skillet. Fry sandwich over medium high heat, pressing down and turning every 2-3 minutes until cheese is melted and bread it golden brown.

Grilled Blue Cheese and Honey Sandwiches

Ingredients (makes 4 sandwiches)

6oz of blue cheese (room temperature, easier for spreading)

4 table spoons of honey

Olive Oil

½ loaf of thick crusty bread


Spread blue cheese on both slices of bread, drizzle honey over the top and sandwich together. Heat olive oil in a skillet. Fry sandwich over medium high heat, pressing down and turning every 2-3 minutes until cheese is melted and bread it golden brown.

Hope you enjoy! This weekend will be spent racing around our lovely little island of Manhattan…literally. My friend is having an “Amazing Race” for her birthday and my competitive nature has already kicked into over drive. After the race it’s up to the Upper East Side for a girls’ night and I’ll be bring some yummy appetizers otherwise known as my next blog post. Then on Sunday we will be sitting on our butts drinking beer watching little Pam-cakes run the marathon, followed by me making something with my leftover half of butternut squash. I know you all will be waiting with baited breath come Monday morning, wondering to yourselves….What’s Elizabeth Cooking Now? Thanks for reading!


2 thoughts on “(Fancy) Grilled Cheese and Tomato Soup

  1. Can you meet me at the finish line with a grilled cheese, the one with onions. This sounds amazing and I have to agree I do love being swaddled by grilled cheese and tomato soup on days like these. Love the blogggg!

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