Slice the Roma tomatoes in half lengthwise. Drizzle the cut sides with extra-virgin olive oil and season generously with sea salt and freshly ground black pepper.

Preheat a grill or grill pan over medium-high heat. Lightly brush the grates with olive oil to prevent sticking. Arrange the tomatoes cut side down on the hot grill and cook for 4 to 6 minutes, or until deep grill marks develop. Carefully flip each tomato and continue grilling for another 3 to 4 minutes, allowing them to soften while maintaining their shape.

Transfer the grilled tomatoes to a serving platter. Sprinkle with an extra pinch of salt and pepper for enhanced flavor. Drizzle with Italian dressing and, if desired, top with freshly grated Parmesan cheese. Garnish with fresh basil leaves and serve immediately for the best taste and texture.