To broil the romaine, turn your oven to the highest Broil setting.
Slice the romaine hearts in half, leaving the bottom intact so the leaves stay together, giving you four halves of romaine. Drizzle each half with olive oil and sprinkle a generous pinch of kosher salt and pepper on both sides.
Place the romaine hearts, cut side down, on a large rimmed baking sheet and broil for 2-3 minutes. Keep a close eye on the romaine as some broilers might work faster than others.
Remove from oven to flip them over and broil the other side for 2-3 minutes. They should come out looking slightly charred, not burnt.
Remove the sheet of romaine from the oven and, using tongs, place the hearts on a serving platter or dinner plates, cut side up. Alternatively, you can give he leaves a rough chop and add to a large salad bowl.
When ready to serve, drizzle dressing over the leaves and garnish as desired.