Preheat your outdoor grill or grill pan to medium medium-low. Brush the cut side of the lettuce with olive oil and grill for 30 to 45 seconds. Lettuce should have grill marks but still remain to be firm and retain it's shape.
Arrange the lettuce, grill marks side facing up, and top with the cherry and tomato halves, feta, pine nuts and pepitas.
Drizzle with the balsamic vinaigrette and sprinkle with cracked black pepper.