Heat 1 tablespoon of olive oil in a sauté pan over high heat. Add the shallots and bacon and cook, stirring occasionally, until the bacon is crispy. If needed, drain off some of the rendered bacon fat. Add cider vinegar, sugar, and stir to combine. Remove from heat, season with salt and pepper, and set aside.
Preheat a grill pan to high heat. Brush the RomaCrunch lettuce with the remaining 2 tablespoons of olive oil. Place on the grill cut side down, and quickly sear.
Serve the RomaCrunch, cut side up, and drizzle the bacon dressing over the top. Sprinkle with blue cheese and garnish with extra cracked pepper.