Preheat outdoor grill to medium heat or preheat broiler.
Bring a pot of salted water to a boil. Blanch the romaine in the salted water for about 30 seconds, or until the central rib is just tender enough to bend. Remove and plunge into ice water to stop the cooking. Drain and pat dry.
Lay romaine leaves out on a counter, outer rib side down. Cut out the wide rib section, or flatten it with your hands. Place a piece of cheese in the middle of each leaf. Top with about 1 tablespoon of the prosciutto. Season with salt and pepper. Make a neat package by folding the leaves around the cheese like an envelope. Place them seam side down. Run a skewers through each package. Brush each with olive oil. Refrigerate if not grilling immediately.
Grill cheese packages over medium heat or broil about 4 inches from the heat. Cook 2 to 3 minutes and turn over. The cheese should begin to weep. Cook another 1 to 2 minutes or until the packets are lightly browned. Top with Sun-dried Tomato Dressing and serve.
In a bowl, mix the sun-dried tomatoes and their oil, vinegar and garlic. Season with salt and pepper.
Recipe courtesy of Michael Chiarello