Grilled Cheese Caesar Salad Recipe

Combine base

In a medium bowl, whisk together 1/2 cup mayonnaise, 1/4 cup plain Greek yogurt and 1/4 cup finely grated Parmesan until smooth.

Add flavorings

Whisk in 1 tsp anchovy paste, 1 tsp Dijon mustard, 2 tbsp fresh lemon juice, 1 tsp Worcestershire sauce and 1 minced garlic clove until fully incorporated.

Emulsify

Slowly drizzle in 3 tbsp extra-virgin olive oil while whisking to emulsify. Season with 1/2 tsp salt and 1/4 tsp freshly ground black pepper. Taste and adjust acidity or salt as desired. Refrigerate while you prepare the rest (at least 10 minutes for flavors to meld).

Heat a large skillet over medium heat and add 1 tbsp olive oil. Add 2 cups day-old bread cubes in a single layer and toss to coat. Cook 4–6 minutes, tossing frequently, until golden and crisp.

Stir in 1/4 tsp garlic powder and 1/4 tsp salt in the last minute of cooking so it adheres. Transfer croutons to a paper towel–lined plate to cool.

Assemble sandwiches: spread softened butter on one side of each of 4 slices of bread. On the unbuttered side of two slices, layer 1/2 cup shredded Gruyère, 1/4 cup shredded sharp cheddar, and one optional Parmesan slice each. Season lightly with black pepper. Top with remaining bread slices, butter side out.

Cook sandwiches: heat a large skillet or griddle over medium-low to medium heat and add 1 tsp olive oil to coat the surface. Place sandwiches in the pan, reduce heat slightly if browning too quickly. Cook 3–4 minutes per side, pressing gently with a spatula, until bread is golden-brown and cheese is melted. If bread is browning before cheese melts, cover pan for 1–2 minutes to trap heat and encourage melting.

Rest and cut: transfer sandwiches to a cutting board and let rest 1–2 minutes. Cut each sandwich diagonally into halves (or quarters) for easier serving.

Prepare greens: place 6 cups torn Romaine lettuce in a large bowl. Add 1/2 cup halved cherry tomatoes if using.

Dress salad: add 3–4 tablespoons of the prepared Caesar dressing to the lettuce and gently toss until leaves are evenly coated. Start with 3 tbsp and add more to taste; you may not need the entire batch.

Add croutons and cheese: sprinkle the pan-toasted croutons over the dressed lettuce and add 2 tbsp freshly grated Parmesan. Toss lightly to combine.

Plate and serve with grilled cheese: divide the dressed salad among 2 plates or a large shallow bowl, place two grilled cheese halves (or one sandwich) alongside or atop the salad as desired. Garnish with extra black pepper and additional Parmesan if you like.