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PdfIn a medium bowl, whisk together the mayonnaise, lemon juice, anchovy paste, Dijon mustard, garlic, salt, and pepper. Slowly drizzle in the olive oil while whisking constantly until the dressing is smooth and emulsified. Stir in the Parmesan cheese and set aside.
Cut each head of romaine in half lengthwise, then cut each half in half again, leaving the core intact so the leaves stay together. Brush the cut sides lightly with olive oil and season with a pinch of kosher salt and black pepper.
Preheat the grill to medium-high heat, about 400°F. Using tongs, carefully oil the grill grates with a paper towel lightly dipped in oil.
Place the romaine wedges cut side down directly on the hot grates and grill until lightly charred, about 1–2 minutes. Turn and grill the other cut side for another 1–2 minutes, just until lightly charred. The lettuce should still be crisp with just a hint of smokiness.
Arrange the grilled romaine on a serving platter. Drizzle generously with the Caesar dressing, additional Parmesan cheese, and a few cracks of freshly ground black pepper. Serve with grilled bread.