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Dill Pickle Sloppy Joe Grilled Cheese

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What happens when you combine a classic Sloppy Joe with a gooey grilled cheese and add a tangy dill pickle twist? You get the most mouthwatering, flavor-packed sandwich ever—the Dill Pickle Sloppy Joe Grilled Cheese!

Ingredients

For the Sloppy Joe Filling:

  • 1 lb ground beef (or ground turkey)
  • ½ small onion, finely diced
  • 2 cloves garlic, minced
  • ½ cup tomato sauce
  • ¼ cup ketchup
  • 1 tablespoon Worcestershire sauce
  • 1 tablespoon brown sugar
  • 1 teaspoon mustard (yellow or Dijon)
  • ½ teaspoon salt
  • ½ teaspoon black pepper
  • ¼ teaspoon smoked paprika (optional, adds a smoky flavor)

For the Sandwich:

  • 8 slices Texas toast or thick sandwich bread
  • 4 tablespoons butter, softened
  • 2 cups shredded cheddar cheese (or slices of cheddar/American cheese)
  • 8-10 slices dill pickles (or more, depending on preference)

Instructions

1. Make the Sloppy Joe Filling

  • In a large skillet over medium-high heat, cook ground beef until browned, breaking it apart (about 5 minutes).
  • Add diced onion and garlic, sautéing until softened (2 minutes).
  • Stir in tomato sauce, ketchup, Worcestershire sauce, brown sugar, mustard, salt, black pepper, and smoked paprika.
  • Let simmer for 5 minutes until the sauce thickens.
  • Remove from heat and set aside.

2. Assemble the Sandwiches

  • Spread butter on one side of each bread slice.
  • Place 4 slices (butter-side down) on a clean surface.
  • Add ½ cup shredded cheddar cheese (or 2 slices) on each bread slice.
  • Spoon a generous portion of Sloppy Joe filling over the cheese.
  • Layer with pickle slices.
  • Add another layer of cheese on top of the pickles.
  • Top with the remaining bread slices (butter-side up).

3. Grill the Sandwiches

  • Heat a large skillet or griddle over medium-low heat.
  • Place sandwiches in the pan and cook for 3-4 minutes per side, pressing lightly with a spatula.
  • Flip carefully and cook until golden brown and crispy, with cheese fully melted.
  • Remove from heat and let rest for 1 minute before slicing.

4. Serve & Enjoy!

  • Cut sandwiches in half and serve immediately.
  • Pair with extra pickles, coleslaw, or a side of crispy fries!

Notes

Tips for the Best Sloppy Joe Grilled Cheese

✅ Use thick bread – Texas toast or sourdough works best for crispy, sturdy sandwiches.
✅ Low & slow grilling – Cooking over medium-low heat ensures perfectly melted cheese without burning the bread.
✅ Don’t skimp on pickles! – The tanginess balances the rich flavors.
✅ Extra saucy? – Add a little more Sloppy Joe sauce before serving.
✅ For a spicy kick – Add sliced jalapeños or a drizzle of hot sauce!

  • Author: niold.com