Sauté the Aromatics: Heat olive oil in a large pot over medium heat. Cook the diced onion for 5 minutes until translucent, then stir in garlic and cook for another minute until fragrant.
Build the Base: Pour in broth and bring to a simmer. Add softened cream cheese, stirring until fully melted and smooth.
Add Flavor and Heat: Mix in shredded cheddar, diced jalapeños, smoked paprika, cumin, salt, and pepper. Let simmer for 10 minutes, stirring occasionally.
Make It Creamy: Stir in heavy cream and heat through. Adjust seasoning as needed.
Prepare the Grilled Cheese Dippers: Butter one side of each bread slice. Place cheddar cheese between two slices, buttered sides out. Grill in a skillet over medium heat until golden brown on both sides. Slice into strips.
Serve: Ladle soup into bowls, garnish with cilantro, and serve hot with grilled cheese dippers.