The Art of Grilled Cheese: Paired with the Perfect Tomato Soup

There’s an undeniable magic in comfort food, especially when the weather decides to play tricks. Even in April, when spring flowers should be blooming, a sudden snowfall can transform the landscape into a whimsical, powdered-sugar wonderland. In such moments, my thoughts invariably turn to the ultimate cozy classic: a warm, gooey grilled cheese sandwich paired with a rich, velvety tomato soup. This combination isn’t just food; it’s a hug in a bowl, a taste of nostalgia that transcends seasons and brings instant warmth.

Perfect Oven Grilled Cheese + The Best Tomato Soup I've Ever Had

While some might raise an eyebrow at a grilled cheese and tomato soup recipe appearing mid-spring, the recent wintery weather has made it feel perfectly fitting. Beyond the current climate, this meal has always held a special place in my heart, evoking cherished memories of spring evenings during my childhood. Sundays were often my mom’s well-deserved break from the kitchen, which meant it was my dad’s turn to whip up something for me. Though he wasn’t a culinary maestro, my dad excelled at two things: crafting a flawless grilled cheese and reheating canned tomato soup like a seasoned chef. Those simple meals, shared on countless spring nights, created a foundation of comfort that I still associate with this delightful pairing.

Discovering Culinary Gold: Jessica Merchant’s “The Pretty Dish”

Today, I’m thrilled to share a recipe for what I genuinely believe is the best tomato soup I have EVER tasted. This incredible creation, known as “Toasted Garlic Tomato Bisque,” comes from Jessica Merchant, the brilliant mind behind the stunning blog How Sweet Eats, and her second cookbook, The Pretty Dish. If you haven’t yet explored her work, prepare to be captivated.

The Pretty Dish, Jessica Merchant

I cannot emphasize enough how highly I recommend this cookbook. We’ve all been there: picking up a cookbook, flipping through its pages, and thinking, “I might make three recipes from this.” But The Pretty Dish is a different breed entirely. It’s a culinary treasure trove where every single recipe sparks excitement. Each page is bursting with creative, utterly doable, and incredibly delicious ideas, all accompanied by truly gorgeous, inspiring photographs. As if that wasn’t enough, it even includes 50 beauty DIYs at the back, making it essentially the only lifestyle book you’ll ever need. It’s a testament to Jessica’s talent that she manages to blend gourmet appeal with home-cook accessibility so seamlessly.

The Best Tomato Bisque, Made Easy

Jessica’s Toasted Garlic Tomato Bisque comes together remarkably quickly, demanding no complicated ingredients or intimidating techniques. In fact, I was able to prepare both this exquisite soup and the grilled cheese in well under an hour. This soup is deeply flavored, incredibly easy to make, and fast enough for any weeknight. Its secret lies in the simple act of toasting garlic to bring out its nutty, sweet notes, which then infuse the entire bisque with an unparalleled depth. The addition of fire-roasted diced tomatoes lends a smoky complexity, while cooking sherry and brown sugar balance the acidity with subtle sweetness. The final touch of heavy cream transforms it into a smooth, luxurious bisque that feels both indulgent and wholesome. I’ve already made this soup three times because it’s that delicious and that simple to perfect!

Perfect Oven Grilled Cheese + The Best Tomato Soup I've Ever Had

The Secret to Perfect Grilled Cheese: An Oven Revelation

Now, let’s talk about the other half of this dynamic duo: the grilled cheese. I confess, for years, I was terrible at making grilled cheese in a skillet. I would inevitably burn the bread, yet somehow the cheese never achieved that perfect, molten state I craved. The result was often a sandwich with overly crunchy, almost painful-to-bite bread and disappointingly unmelted cheese in the center. It was a constant source of kitchen frustration.

My accidental breakthrough came when I unknowingly bought extra-thick, fluffy bakery bread. My husband, Grant, pointed out (rightly so) that such thick bread was practically destined to burn in a pan before the cheese even had a chance to properly melt—a familiar scenario for me, unfortunately. However, this seemingly inconvenient purchase led to one of my best kitchen discoveries to date! I decided to experiment by making the grilled cheese in the oven, under the broiler. My goal was to achieve that golden-brown crust and perfectly melted interior without the dreaded burnt bread.

The results were nothing short of miraculous! It worked like an absolute charm. The oven broiler method delivers a beautifully toasted exterior while allowing the cheese ample time to become wonderfully gooey and melted, all without any risk of scorching. Grant and I happily devoured our perfectly crafted grilled cheese and this incredible tomato soup, reveling in the success of this newfound technique. This method not only bypasses the common pitfalls of stovetop grilling but also creates a consistently delicious, evenly cooked sandwich every time. It’s a game-changer for anyone who struggles with the traditional method or simply wants to streamline the process for multiple sandwiches.

Perfect Oven Grilled Cheese + The Best Tomato Soup I've Ever Had

I even convinced Grant to lend a hand for the classic “cheese pull” photo above, as I, sadly, am not equipped with three hands. I think he absolutely nailed it – don’t you agree? Perhaps a future in hand-modeling awaits him! But all jokes aside, the important takeaway here is that you absolutely need to experience this ultimate comfort meal.

Your Invitation to Indulgence: Make This Comfort Food Duo

This dynamic duo of toasted garlic tomato bisque and oven grilled cheese is more than just a meal; it’s an experience. The creamy, savory warmth of the soup perfectly complements the crispy, cheesy goodness of the sandwich. Every bite is a journey back to simpler times, a comforting embrace that can brighten even the dreariest of days. Whether you’re battling an unexpected chill, seeking a taste of nostalgia, or simply craving an undeniably delicious and easy meal, this pairing is your answer.

  • Be sure to explore How Sweet Eats for more of Jessica Merchant’s fabulous and inspiring recipes.
  • Treat yourself to a copy of The Pretty Dish because it truly is the most amazing cookbook I have encountered in a very, very long time. It will undoubtedly become a staple in your kitchen.
  • Most importantly, make, eat, and fall in love with this incredible tomato soup and this perfectly melty grilled cheese!
  • Consider buying enough ingredients to make the soup twice. Trust me, you *will* want to have leftovers or another batch ready to go; it’s that good and freezes beautifully.

That’s all for today, folks! I sincerely hope the weather is glorious wherever you are. But if it’s not, well, you now have the perfect reason to treat yourself to these heartwarming recipes. As always, if you decide to make this or any other recipe from my kitchen, I’d absolutely love to see your creations! In this particular case, please tag your delicious photos with both #bluebowlrecipes AND #theprettydish so we can all share in the comfort food joy.

A huge thank you, Jessica, for creating such a stunning cookbook and for giving me (and now you!) my new favorite tomato soup recipe. It’s a true culinary gift!

Perfect Oven Grilled Cheese + The Best Tomato Soup I've Ever Had

Grilled Cheese and Tomato Soup

5 from 6 votes

A Better Way To Make Grilled Cheese + The Best Tomato Soup I’ve Ever Had

By
Stephanie Simmons
Perfectly toasty and melty grilled cheese made in the oven, served with the most amazing tomato soup ever – Toasted Garlic Tomato Bisque from Jessica Merchant’s new cookbook, The Pretty Dish!
Prep:

10 minutes

Cook:

35 minutes

Total:

45 minutes

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Ingredients

  • FOR THE TOMATO SOUP
  • 2 tbsp butter, salted or unsalted works
  • 4 cloves garlic, thinly sliced
  • 2 shallots, sliced, The shallots I bought were very large, so I only used one
  • 1 1/2 tbsp tomato paste
  • 1 28 oz. can fire-roasted diced tomatoes
  • 2/3 cup cooking sherry
  • 1/3 cup chicken stock, Vegetable stock works too, if you want to make this recipe vegetarian!
  • 3 tbsp brown sugar
  • 1/2 tsp dried basil
  • 1/4 tsp salt
  • 1/4 tsp black pepper
  • 3/4 cup heavy cream, Plus a little extra for garnish
  • fresh basil and oregano, chopped, For topping
  • FOR THE GRILLED CHEESE
  • 1 loaf of good bakery bread
  • 6 oz cheese, We used a mix of gruyere and mild cheddar, and we used blocks of cheese and cut slices
  • 1/4 cup butter

Instructions

  • Make the soup: In a medium saucepan (or Dutch oven), melt the butter over medium-low heat. Add the thinly sliced garlic and cook, stirring often, until it turns a beautiful golden brown and becomes delightfully toasty. Using a slotted spoon, carefully transfer the toasted garlic to a plate and set aside. Next, add the sliced shallots to the same pan and cook, stirring occasionally, for 8 to 10 minutes, or until they are soft, translucent, and slightly golden. Stir in the tomato paste and cook for an additional 5 minutes, allowing its flavors to deepen. Return the reserved toasted garlic to the pan, along with the fire-roasted diced tomatoes, cooking sherry, chicken stock (or vegetable stock for a vegetarian option!), brown sugar, dried basil, salt, and black pepper. Bring the entire mixture to a gentle boil, then reduce the heat to a simmer and let it cook for 20 minutes, allowing all the flavors to meld and intensify.
  • Once the soup has finished simmering, carefully transfer it to a high-powered blender. Blend until the soup is perfectly smooth and pureed to your desired consistency. Return the velvety smooth soup to the pot and gently heat over low heat. Just before serving, stir in the heavy cream, which will add a luxurious richness and creamy texture. Taste and adjust seasoning with additional salt and pepper if desired.
  • Make the grilled cheese: Turn on your oven’s broiler. Generously spray a baking sheet with non-stick spray, ensuring even coverage. Slice your good bakery bread into desired thickness. Spread a thin layer of butter on both the outsides and the insides of each slice of bread. Lay two slices of bread onto the prepared baking sheet. Evenly distribute half of your chosen cheese mixture (like Gruyere and mild cheddar) onto each slice of bread. Place the baking sheet with the bread and cheese into the oven under the broiler for 1 to 2 minutes, without adding the top pieces of bread. It’s crucial to keep a very close eye on the sandwiches during this step, as broilers are powerful and can toast quickly! After 1-2 minutes, remove the baking sheet, add the top slice of bread to each of the two cheesy pieces, and return to the oven for another 1 to 2 minutes. Carefully flip the sandwiches and broil for a final 1 to 2 minutes on the other side. Again, constant vigilance is key here to prevent burning; you’re looking for a beautiful golden-brown crust and perfectly melted cheese.
  • Before serving, drizzle the warm tomato soup with a little extra heavy cream for an elegant touch, and garnish with freshly chopped basil and oregano. Serve immediately with the hot, perfectly toasted, and melty grilled cheese sandwiches. Enjoy this ultimate comfort food experience!

Nutrition


Calories:
328
kcal

Nutrition information is automatically calculated, so should only be used as an approximation.





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