1 and 1/2 pounds eggplant (about 4 medium), cut into 1-inch cubes
5 tablespoons extra-virgin olive oil, more as needed
1/2 teaspoon kosher salt, more as needed
1/4 teaspoon black pepper, more as needed
1 very large ripe tomato, cored and diced (1 and 1/2 cups)
1/2 pound dried penne
3 garlic cloves, peeled and smashed
3 anchovy fillets
Large pinch chile flakes
2 tablespoons drained capers
Freshly squeezed lemon juice
1/4 cup torn basil leaves
2 tablespoons torn mint leaves
2 tablespoons finely chopped chives
Heat oven to 400 degrees. On rimmed baking sheet, toss together eggplant, 3 tablespoons olive oil, 1/2 teaspoon salt and 1/4 teaspoon pepper. Spread into one layer. Roast, tossing occasionally, until the eggplant is golden brown, about 25 minutes.
Place tomato in large bowl and sprinkle lightly with salt.
Bring large pot of salted water to a boil. Cook penne to al dente according to package instructions; drain well.
While pasta cooks, heat large skillet over medium-high heat. Add 2 tablespoons oil. Stir in garlic, anchovies and chile flakes, and cook until golden and soft, about 3 minutes. Turn off heat and, using slotted spoon, transfer garlic to cutting board. Let garlic cool for a few minutes, then chop up and add back to the oil. Pour garlic-chile into bowl with tomatoes. Add eggplant and capers, and toss well.
Add pasta to bowl with eggplant and tomatoes. Season with salt, pepper and lemon juice to taste, and drizzle generously with oil. Toss in herbs and serve warm or at room temperature.