Grilled Cheese Recipe

Prepare tomatoes

If you have a grill or smoker, lightly char the diced roma tomatoes over medium-high heat for 3–4 minutes until edges are blistered; alternatively, broil for 4–5 minutes, turning once. This adds a smoky note. Transfer to a bowl.

Heat 1 tablespoon olive oil in a medium skillet over medium heat. Add the chopped onion and sauté 4–5 minutes until translucent.

Add the minced garlic and cook 30 seconds until fragrant, then add the charred tomatoes to the skillet.

Stir in brown sugar, apple cider vinegar, smoked paprika, red pepper flakes, salt, and black pepper. Reduce heat to low and simmer gently, stirring occasionally, 10–12 minutes until mixture thickens. If mixture becomes too dry, stir in up to 2 tablespoons water to reach a jammy consistency.

Taste and adjust seasoning. Remove from heat and let cool slightly; chutney will thicken as it cools. This yields enough for 4 sandwiches and can be made ahead and refrigerated up to 5 days.

Combine shredded sharp cheddar and pepper jack in a bowl and toss to mix evenly.

Spread about 1/2 tablespoon softened butter on one side of each bread slice (butter side will be the exterior). For a richer crust, also lightly butter the inside of the bread in addition to the exterior if desired.

Place 4 bread slices butter-side down on a work surface. Top each with a generous layer (about 3/4 cup) of the mixed cheeses, leaving a small border to avoid overflow.

Spoon about 2 tablespoons smoked tomato chutney evenly over the cheese on each sandwich. If using basil, tear a leaf or two and place over chutney.

Top with remaining bread slices, butter-side up, pressing gently to compact.

Heat a large nonstick or cast-iron skillet over medium-low to medium heat. Add 1 tablespoon melted butter and swirl to coat the pan.

Place assembled sandwiches in the skillet (work in batches if needed). Cook 3–4 minutes on the first side until golden brown and cheese begins to melt. Press down gently with a spatula or a bacon press for even contact.

Flip sandwiches and cook another 2.5–4 minutes until second side is golden and cheese is fully melted. If crust browns too quickly before cheese melts, reduce heat to low, and cover the pan for 1–2 minutes to help cheese melt through.

Transfer sandwiches to a cutting board and let rest 1 minute. Slice in half on the diagonal and serve immediately with extra chutney on the side if desired.