Heat 1/2 teaspoon olive oil in a medium cast-iron skillet over medium-low heat. Add the garlic to the skillet and cook for 1 minute, stirring. Remove from the skillet and transfer to a small bowl. Add 2 tablespoons olive oil to the skillet, increase the heat to medium-high, and add the broccolini. Season with salt and pepper and cook for 2 minutes. Turn over the broccolini and cook for an additional 2-3 minutes or until slightly charred. Remove from the skillet and set aside in a warm place.