Divide the sliced bananas among the four glasses, smash slightly and fill each glass with 3/4 cup of milk. Refrigerate until ready to serve.
Combine the broccoli and 1 tablespoon water in a microwave-safe bowl. Cover with plastic wrap and microwave until crisp-tender, about 2 minutes. Let rest for a few minutes, carefully remove the plastic and drain.
Tear up one slice of bread into small pieces and soak in the remaining 1/3 cup milk in a large bowl until soft, about 2 minutes. Add the broccoli, cheese, basil, eggs, 1/2 teaspoon salt and some pepper. Heat half of the oil in a medium nonstick pan over medium heat. Pour in the egg mixture and cook until the bottom begins to set, about 2 minutes. Adjust the heat to medium-low, cover and continue to cook until the middle is set, 6 to 7 minutes more.
Meanwhile, toast the remaining bread, then rub each slice with garlic and top with a slice of tomato. Drizzle the toast with the remaining 1/2 tablespoon oil.
Cut the frittata into four slices and divide among four plates along with the tomato toast. Serve with the banana milk.