### Instructions
**For the Creamy Tomato Soup:**
1. **Sauté Aromatics:** Heat olive oil in a large pot or Dutch oven over medium heat. Add the chopped onion and cook until softened and translucent, about 5-7 minutes. Add the minced garlic and cook for another minute until fragrant.
2. **Add Tomatoes and Seasonings:** Stir in the crushed tomatoes, diced tomatoes (with their liquid), vegetable broth, dried basil, dried oregano, red pepper flakes (if using), and sugar. Bring the mixture to a simmer.
3. **Simmer and Blend:** Reduce heat to low, cover, and simmer for at least 20-25 minutes, allowing the flavors to meld. For a creamier, smoother soup, carefully use an immersion blender to blend the soup directly in the pot until desired consistency is reached. Alternatively, transfer the soup in batches to a regular blender (be very cautious with hot liquids and vent the lid) and blend until smooth. Return the soup to the pot if using a regular blender.
4. **Finish with Cream and Season:** Stir in the heavy cream. Season with salt and freshly ground black pepper to taste. Heat gently for a few more minutes, but do not boil after adding the cream.
**For the Grilled Cheese Dippers:**
1. **Prepare Bread:** Butter one side of each slice of bread generously.
2. **Assemble Sandwiches:** Place four slices of bread, butter-side down, on a clean surface. Layer two slices of cheese on each. Top with the remaining four slices of bread, butter-side up.
3. **Grill:** Heat a large non-stick skillet or griddle over medium-low heat. Place the sandwiches in the skillet (you may need to do this in batches). Cook for 3-5 minutes per side, or until the bread is golden brown and crispy, and the cheese is melted and gooey.
4. **Slice and Serve:** Once cooked, remove the grilled cheese sandwiches from the skillet. Allow them to cool slightly, then slice each sandwich into 2-3 long “dippers” or “fingers.”
**To Serve:**
Ladle the hot creamy tomato soup into bowls. Arrange the grilled cheese dippers alongside or directly in the soup. Garnish with fresh basil leaves if desired. Enjoy immediately!
### Short Tips
* **For richer flavor:** Roast your fresh tomatoes with a little olive oil, salt, and pepper before adding them to the soup.
* **Bread choice matters:** A sturdy sourdough or a good quality white bread holds up well for dipping.
* **Cheese blends:** Experiment with different cheese combinations for your dippers, like a mix of Gruyere and sharp cheddar, or Colby Jack and provolone.
* **Make ahead:** The tomato soup can be made a day in advance and reheated gently. Add the cream just before serving.
* **Kid-friendly option:** For picky eaters, ensure the soup is very smooth and serve the grilled cheese cut into fun shapes using cookie cutters.
