This past weekend was rainy and cold, and it felt like fall was finally here. The leaves are starting to deepen into bright yellows and oranges and dark rain clouds we had all weekend made for gorgeous contrasts – the colors were even more brilliant against an almost purple-grey sky. Unfortunately we were more concerned with staying cozy and warm inside than getting out to take photos. 
Both the rainy weather and the fact that we’d both been traveling a lot and finally had a weekend home together made us just want to snuggle up and enjoy some quiet time. We even pulled out a puzzle! So when it came time for dinner on Saturday we both wanted something really comforting and warm. I came across this recipe for grown-up grilled cheese last week and had been craving it ever since. I couldn’t imagine it without tomato soup and since we’d just stocked up on a whole crate of tomatoes from the farmer’s market to can this week, it was easy to throw a fresh soup together. 
To make the grilled cheese you want to sauté thinly sliced onions slowly on low heat for a nice long time to caramelized them, bringing out all of their sweetness. This recipe calls for a little sugar and balsamic vinegar to enhance the flavors even more. 
Half way there….
While your grilled cheese onions are slowly caramelizing, wash and chop your tomatoes….roma tomatoes are probably best for flavor but we used what we had and it was great. Spread the chopped tomatoes out on a cookie sheet, drizzle a little olive oil and salt and pepper over them and roast in the oven for 20-30 minutes until they are softened, slightly browned and the juices are leaking out of them. 
About 10 minutes before the tomatoes are finished roasting, dice another medium onion. Warning…this meal uses a lot of onions! If you are like Ta’u and start to cry the minute one is cut into, get out your goggles, or get out of the room while the non-affected partner takes charge of chopping onions (like me). Sauté the chopped onion along with garlic and red pepper flakes until the onion softens, about 3-4 minutes. This is the beginning of your tomato soup base. Add broth and a can of chopped tomatoes and then carefully stir in the roasted tomatoes. 
It’s starting to come together. You want to simmer it over low heat for about 30 minutes. While that’s going on, begin to prepare your grilled cheese sandwiches. Start with good sourdough bread…I know some people aren’t thrilled about white bread, but trust me it really makes the meal. It’s comfort not health we’re going for right? 
Butter one side of each slice of bread and on the non-buttered sides layer slices of cheddar cheese and baby kale (stems removed). Then add the caramelized balsamic onions. 
Heat a pan slowly and add the sandwiches. We always used to burn grilled cheese sandwiches because we’d get impatient and turn up the heat. Luckily you have the soup to wait for so you have some time….take it easy and heat the sandwiches slowly, covered, in a sauté pan or cast iron skillet, and you will get that perfectly browned finish. 
Now, while the sandwiches are finishing up, get out your immersian blender. If you have one, this is the perfect moment to use it. 
If you don’t have an immersion blender, a regular old blender works great too, just be careful not to over fill it. Seeking comfort does not include third degree burns from soup exploding from a blender, right? Puree the soup until it is a nice smooth consistency. 
Add about 1/4 c. cream to smooth out the taste and chopped basil to give it more flavor. Add more salt and pepper to taste. Meanwhile keep checking those sandwiches and turning them as they get browned on each side. 
And there you have a yummy comforting meal, with a grown-up twist that proves you don’t have to sacrifice flavor and fresh ingredients to get that feeling. Now, time on the other hand, might be sacrificed a bit…this definitely isn’t a fast 10 minute meal, but if you double the soup recipe and double or triple the onions you caramelize, you can have this meal all week, and the second time around, it is a 10 minute meal.
Creamy Tomato Basil Soup
Adapted from Two Peas and Their Pod
Serves 4 (double it for lots of leftovers)
Ingredients:
- 2 ½ lbs Roma tomatoes, chopped
- 4 Tbsp olive oil, divided
- 1 medium onion, chopped
- 2 cloves garlic, minced
- Pinch or two of red-pepper flakes
- 1 (15 oz.) can diced tomatoes
- 4 c. vegetable broth or chicken broth
- ¼ c. heavy whipping cream
- ¼ c. chopped basil
- Salt and pepper to taste
Preheat oven to 400 degrees F. Wash and chop tomatoes and spread them on a baking sheet. Drizzle with up to 2 Tbsp olive oil and sprinkle with salt and pepper. Roast in the oven for 20-30 minutes until softened, starting to brown, with juices spilling out.
Just before tomatoes are finished roasting, heat 2 Tbsp olive oil in a large pot over medium heat. Add the chopped onions and cook until tender about 2-3 minutes. Add the garlic and red pepper flakes and cook another 2 minutes or so, being careful not to burn the garlic. Add the canned tomatoes and broth. Then, remove the roasted tomatoes from the oven and carefully add them to the pot. Simmer the soup over medium-low heat for about 30 minutes.
Using an immersion blender, puree the soup in the pot. Or, transfer it to a blender, being careful not to overfill it, so as to avoid explosions. If you used a blender to puree the soup, return the soup to the pot. Add ¼ c. heavy whipping cream and stir in almost all of the chopped basil. Reserve a small amount to top each bowl with after serving. Season the soup with additional salt and pepper to taste.
Soup will last up to a week in the refrigerator or up to a month in the freezer.
Grilled Cheese Sandwiches with Caramelized Onions and Baby Kale
Adapted from Just a Taste‘s recipe featured on A Cup of Joe
Makes 2 large sandwiches
For the caramelized onions:
- ½ Tbsp butter
- 1 tsp oil
- 1 large onion, thinly sliced
- 1/2 tsp salt
- 1/8 tsp black pepper
- 1 tsp sugar
- 2 Tbsp balsamic vinegar
For the grilled cheese:
- 1 Tbsp unsalted butter
- 4 slices sourdough bread
- 4 slices sharp cheddar cheese
- 1 c. baby kale leaves (spinach would work great too)
For the onions: Heat the butter and oil in a saucepan over medium-low heat. Add the onions and salt and pepper and cook, stirring regularly, until the onions soften, about 10 minutes. Add the sugar and continue cooking 5 minutes more. Add the balsamic vinegar and reduce heat to low. Cook, stirring occasionally for 15 minutes until the onions are very soft and darkened.
For the grilled cheese: Butter one side of each slice of bread. On the non-buttered side of the bread, stack one slice of cheese, then top it with half the caramelized onions and half the kale leaves. Then top that with a second slice of cheese, and finally the second slice of bread with the non-buttered side touching the cheese. Repeat for the second sandwich.
Slowly heat a sauté pan or cast iron skillet over medium to medium-low heat. Add each sandwich and cover with a lid. Heat until the bread is nicely browned, then flip and repeat on the other side. There isn’t a good measure of time for this because it depends on the amount of heat and type of pan you use, so just keep checking them every few minutes to avoid burning. When both sides of the bread are toasted, the cheese should be melty and the kale should be wilted.
Remove from the pan and serve.