Grilled Cheese Roll Ups with Homemade Tomato Soup Dipping Sauce: A Fun & Flavorful Twist on a Classic

The timeless combination of grilled cheese and tomato soup has long been a source of comfort and joy. It’s a meal that evokes childhood memories, cozy evenings, and simple pleasures. But what if we told you there’s a way to elevate this beloved classic, making it even more exciting, interactive, and utterly irresistible? Enter **Grilled Cheese Roll Ups with Homemade Tomato Soup Dipping Sauce** – a playful and delicious twist that promises to transform your dinner routine from mundane to magnificent. This isn’t just a meal; it’s an invitation to rediscover the fun in food, a perfect excuse to “play with your dinner” and delight your taste buds, making every bite a mini adventure.

Life has a funny way of throwing curveballs, and sometimes, those unexpected shifts lead us down paths we never anticipated. For many, career changes or big moves bring a whirlwind of uncertainty. Just a short while ago, I found myself navigating such a period – two months since leaving my job, and a little over a month since returning to Pittsburgh. It felt like an eternity and a blink of an eye all at once. During times like these, the pressure to succeed and the quiet anxiety of the unknown can be overwhelming. There’s a constant internal battle, pushing hard for new opportunities while facing the reality of a competitive world. You want to shout, “Hey, look at what I can do!” but often, it feels like you’re barely making a ripple. The questions from well-meaning friends and family about “how things are going” can be tough when you’re still finding your footing. And the whispers, real or imagined, about being “lazy” or “unemployed” sting, especially when you’re working tirelessly behind the scenes.

I know success isn’t built overnight, but patience isn’t always my strongest suit, particularly when navigating feelings of uncertainty and doubt. It’s a stressful journey, trying to figure out the next chapter. (Speaking of which, you can see some of the work I’m passionate about at my online portfolio, which I revamped in August). Yet, amidst these challenges, a wonderful silver lining emerged: a renewed passion for cooking. Before, exhaustion often overshadowed the joy of creating in the kitchen – a long day at work, a rushed dinner, then straight to blogging. Now, even with relatively quick meals, I have the energy and mental space to truly enjoy the process. And when you genuinely enjoy cooking, that creativity sparks. It was in this joyful space that the genius idea of Grilled Cheese Roll Ups with Tomato Soup Dipping Sauce was born. Just when you thought grilled cheese and tomato soup couldn’t possibly get any better, this innovative approach proves it absolutely can. Oh, it so does.

The Inspiration: From Sweet to Savory Roll Ups

The concept of “roll ups” isn’t entirely new to my kitchen. I’ve previously explored the delightful world of sweet French toast roll ups, creating popular versions like Apple Butter French Toast Roll Ups with Apple Butter Cream Cheese Dipping Sauce and Pumpkin Cheesecake French Toast Roll Ups with Pumpkin Spice Dipping Sauce. These sweet treats sparked an idea: why not apply the same fun, roll-up technique to a savory dish? The moment the thought clicked – bread, cheese, GRILLED CHEESE! – the path became clear. And what could possibly be a more perfect accompaniment to grilled cheese than a rich, warm tomato soup, made just right for dipping? It’s a natural evolution of a beloved duo, transforming it into an exciting, hand-held experience that’s both nostalgic and novel. These roll ups offer all the comforting flavors you love in a format that’s simply more enjoyable and less messy.

Crafting the Perfect Tomato Soup Dipping Sauce

The secret to these roll ups truly shines with the accompanying dipping sauce. This isn’t just any tomato soup; it’s a specially adjusted version, thickened to the perfect consistency for dipping. My inspiration came from my Chicken Parmesan Meatball Soup recipe, but with a crucial twist: no meatballs, and a reduced amount of broth. This modification ensures the sauce is robust and flavorful enough to stand on its own, clinging beautifully to each crispy roll up without being watery. You’ll want a sauce that offers a satisfying dip, providing that familiar tangy warmth that perfectly complements the salty, melty cheese. For a truly authentic flavor, consider using fresh, ripe tomatoes when they’re in season, enhancing the sweetness and vibrancy of the sauce. However, high-quality canned diced tomatoes work wonderfully year-round, making this recipe accessible no matter the season. The simplicity of transforming a classic soup into a decadent dipping sauce is pure culinary magic, and it’s what makes this dish truly extraordinary.

Why These Roll Ups Are a Game Changer: Convenience and Fun

One of the many fantastic aspects of this recipe is its versatility and convenience. You can easily fry about four roll ups at a time, stacking them onto a plate to serve a crowd. Imagine the delight of serving these during your favorite football game on TV – a less messy, more interactive alternative to traditional grilled cheese sandwiches that everyone can enjoy. They’re also an ideal fun after-school snack for kids before heading off to practice, providing a satisfying and exciting treat that fuels them up. Or, if you live by yourself, like me, there’s absolutely no shame in hoarding all the roll ups for yourself! They make a perfect comfort meal for one, ready whenever you are. The dipping sauce is a dream for meal prep; it stays fresh in the fridge for about a week. And since grilled cheese isn’t known for being a great leftover (trust me, a soggy cold grilled cheese is never ideal), you can simply fry up a few roll ups as needed and reheat the sauce. This means a delicious, hot dinner can be on the table in under 30 minutes, even on the busiest weeknights. It’s truly a recipe designed for both ease and enjoyment, transforming a simple concept into a memorable meal.

Grilled Cheese Roll Ups With Tomato Soup Dipping Sauce

Yield:
12 roll ups

The dipping sauce can be made ahead of time and stored in the refrigerator for a week.

Ingredients

Tomato Soup Dipping Sauce

• 1 tablespoon olive oil
• 1/4 cup chopped onion (roughly half a small onion)
• 1 clove minced garlic
• 1 teaspoon sugar
• 1/4 teaspoon salt
• 1/4 teaspoon black pepper
• 1/4 teaspoon dried basil
• 1/4 teaspoon dried oregano
• 1/4 teaspoon thyme
• 14 ounces canned diced tomatoes with juices
• 1 cup vegetable or chicken broth
• 1 teaspoon balsamic vinegar

Grilled Cheese Roll Ups

• 12 slices white bread
• 12 slices American cheese
• 4 tablespoons melted butter (add pinch of salt if unsalted)

Instructions

For the sauce

1. In a large Dutch oven, heat up the oil until hot. Add the onion and cook until soft, 5-8 minutes. Add the garlic and cook 1 minute. Add the sugar, salt, pepper, basil, oregano, and thyme. Stir all together and cook another 5 minutes. Add the tomatoes, broth, and vinegar. Bring a boil then turn down to a simmer and cook 30 minutes.
2. Add the soup mixture to a blender and puree until smooth. Be careful – because the mixture is hot, it will expand greatly in the blender when you turn it on. If needed, puree in two batches.

For the roll ups

1. Flatten one slice of bread to about half of its original thickness. Add one slice of cheese. Roll up bread and set aside, seam side down. Repeat with the remaining bread.
2. Heat a skillet over medium heat. Dip each roll up into the butter. Once hot, turn the heat down to medium-low and add several roll ups without overcrowding (my skillet cooked 4 at a time). Cook until the cheese has melted and the bottom is golden brown* then flip. Cook until golden brown then transfer to a plate. Repeat with remaining roll ups. Serve hot with dipping sauce.

Notes

*The key to melting the cheese without burning the bread is cooking on low heat. If the cheese is a bit thick, cover with a lid to help speed up the process.

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