In a large skillet, lay bacon flat with little overlap before turning on heat.

Cook over medium heat, turning the bacon every 2–3 minutes. Turn the bacon until it reaches an internal temperature of 145°F, about 7–12 minutes total.

Transfer bacon to a paper towel-lined plate to cool.

Preheat the grill to 400°F or high heat. Clean and oil the cooking grate, then close the lid.

Cut romaine heads in half, lengthwise.

Slice bread in ½-inch thick slices.

Drizzle olive oil over both sides of the bread slices and all over the romaine heads. Season everything with pepper.

Place bread on the grill. Turn the slices occasionally until the bread is toasted with a little bit of char, about 3–5 minutes. Remove from heat and cut into cubes.

Place romaine heads on the grill and cook for 1–2 minutes on each side until slightly charred. Remove to serving plates.

Drizzle lettuce with dressing, getting between all the leaves. Top with croutons and crumbled bacon, then serve!