preheat oven to 425. In an 8-inch square baking dish, toss cherry tomatoes with 3 Tablespoons oil, season with salt and pepper. Roast until bursting and charred in spots, 20-30 minutes. Meanwhile, on a rimmed baking sheet, toss bread with 2 Tablespoons of oil and Pecorino Romano, season with salt and pepper. Roast, tossing halfway through, until golden brown and crisp, about 12 minutes.
Toss diced tomatoes, basil, and mint with remaining 2 Tablespoons of oil; season with salt and pepper. Bring a large pot of salted water to a boil. Add pasta; cook according to package directions until al dente. Reserve 1 cup liquid; drain.
Return pasta to pot, toss with roasted tomatoes, their oil and 1/2 cup of reserved water. Season with salt and pepper. Divide among plates then give each a dollop of ricotta, a spoonful of fresh-tomato mixture, and a sprinkle of croutons. Serve, garnished with a sprig or two of herbs, a generous drizzle of oil, and some cheese and pepper.