For the croutons: Preheat the oven to 375 degrees F. Drizzle the bread with olive oil. Using a small heart-shaped cookie cutter, cut out pieces of the bread and place on a baking sheet. Bake until crispy and golden, 8 to 10 minutes. Set aside to cool.
For the vinaigrette: In a blender, combine the raspberries, oil, chocolate-balsamic vinegar, honey, salt and pepper. Blend until smooth.
Place the wedges of lettuce on 4 plates and drizzle with the vinaigrette. Top with the chopped chocolate and croutons before serving.