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Preheat the oven to 350˚F.
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Combine garlic, lemon juice, the ¼ cup olive oil, salt and pepper in a small jar with a tight fitting lid. Set aside.
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Put the regular couscous in a bowl with ¼ teaspoon kosher salt and 1 teaspoon olive oil. Add ⅔ cup boiling water, stir and cover the bowl with plastic wrap. Set aside for 12 minutes, then remove plastic wrap and separate the grains with a fork. Set aside to cool.
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Bring a medium size pot of boiling water to a boil. Add 1 teaspoon salt, 1 teaspoon olive oil and Israeli couscous. Cook for 8 minutes or until al dente. Drain in a colander and rinse under cold running water. Allow to cool.
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Meanwhile, spread the quartered vine tomatoes over half of a large baking pan and sprinkle with the brown sugar, balsamic vinegar, 2 tablespoons olive oil, ¼ teaspoon kosher salt and a generous grind of black pepper. Place in the oven and bake for 20 minutes, then remove pan from the oven and increase the temperature to 400F. On the empty side of the baking pan, spread the yellow tomatoes. Season them with ⅛ teaspoon kosher salt, freshly ground black pepper and 1 tablespoon olive oil. Return to the oven and roast for 12 minutes longer.
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Remove the tomatoes from oven and allow to cool. Mix together the regular couscous and the Israeli couscous (pearl pasta) in a large bowl. Add the dressing, herbs, cooked tomatoes with all their juices, and the small fresh tomatoes. Very gently mix together using your hands. Taste for seasoning: add salt and pepper as needed.