The OG Couple Goals: A Creamy Tomato Basil Soup and a deliciously cheesy Grilled Cheese Sandwich is the ultimate Valentine’s Day (or Galentine’s Day) meal, am I right? Fresh Roma tomatoes and garlic roasted to perfection then made into a creamy soup and served with a melty gruyere and cheddar grilled cheese is enough to make anyone want to ride straight into the sunset. It’s simple, classic, and made with love!

My husband, Jaime, and I made a last-minute decision to head up to Broken Bow, OK for a little early Valentine’s Day retreat. And since we live in a small, poorly-lit, apartment, I knew I wanted to take advantage of the rental’s full-sized kitchen to cook us up something yummy.
I knew whatever I put on the menu needed to be something simple while still feeling intentional and cozy. Enter- Tomato Soup and Grilled Cheese. It ended up being the perfect choice since it was dark and stormy the entire time we were there. There’s nothing quite like snuggling up on the couch with a hot bowl of soup and delicious grilled cheese while it’s freezing cold and pouring rain outside.
We even decide to film the first couple of episodes of my lifestyle show (title TBD). However, filming proved to be a bigger fish to catch than we anticipated. We are filmmakers by trade, but this was definitely a learning experience. To be honest- it turned out exactly how I hoped it wouldn’t: a tutorial. But alas, ’twas just the first couple episodes of many, I hope. Can only go up from here, right? You can watch that episode below!

Roasted Tomato Soup and Grilled Cheese Sandwich
Equipment
- Dutch oven or Soup Pot
- Immersion Blender or regular blender
Ingredients
Tomato Soup
- 10 Roma Tomatoes sliced lengthwise
- 4 Garlic Cloves
- 3 tbsp Olive Oil
- 1 Yellow Onion chopped
- 1 tbsp Thyme fresh
- 1 28oz can San Marzano Tomatoes Crushed
- 1 tsp Kosher Salt
- 1/2 tsp Ground Black Pepper
- 1 cup Basil Fresh
- 1 tbsp granulated sugar
- 2 cups Chicken Stock
- 2/3 cup Heavy Cream
Grilled Cheese
- 2 slices Sourdough bread
- 2 tbsp Mayonnaise
- Dijon Mustard optional
- 1 tbsp unsalted butter
- 1/3 cup Gruyere Cheese freshly grated
- 1/3 cup Cheddar Cheese freshly grated
Instructions
Tomato Soup
- Preheat oven to 375℉.
- Slice tomatoes lengthwise and lay them face up on a baking sheet. Add garlic cloves. Drizzle with olive oil and then sprinkle with salt and pepper.
- Roast tomatoes for 1 hour. Remove from oven and set aside.
- Heat 2 tbsp of olive oil in a large pot (or Dutch oven) over medium-high heat.
- Add chopped onion and saute for about 5 minutes, or until onion is translucent.
- Stir in Thyme, salt, and pepper. Saute for 1 minute.
- Add can of crushed tomatoes, basil, and sugar to the pot. Lower heat and simmer for about 10 minutes.
- Add the chicken stock and the roasted tomatoes and garlic to the pot and simmer for 30 minutes, stirring occasionally.
- Remove the soup from heat. Using an immersion blender, puree the soup until smooth.
- Stir in the cream.
Grilled Cheese
- Place the bread slices on a cutting board and spread 1 Tbsp of mayonnaise to the top side of each slice. Flip one slice of bread over to its other side. Spread a thin layer of Dijon Mustard. Layer the Cheddar and Gruyere cheeses over the mustard, then place the other slice of bread, mayo-side out, on top of the cheese.
- Heat a non-stick skillet over medium-low heat. Melt just enough butter to coat the bottom of the pan. Place the sandwich in the pan and cover with a lid. Cook for about 2-4 minutes, or until the bottom of the sandwich is a nice golden brown. Flip, then replace the lid and cook for another 2-4 minutes or until golden brown and the cheese is melty.
Notes
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