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1
Preheat oven to 400 degrees F. Pour 1 tablespoon of the oil into a baking dish big enough to fit all the tomatoes in one layer. Place tomatoes cut side facing up; pour the remaining tablespoon oil over the top of each tomato; sprinkle with salt, sugar and red pepper flakes. Scatter the garlic cloves in-between the tomatoes.
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2
Place the baking dish on the middle rack of the oven and roast for about 1 hour; turn tomatoes over half way of roasting. When the tomatoes are soft and their skin is lightly chard, remove from oven and let cool.
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3
When cool enough to handle, peel of the skins from tomatoes and garlic cloves and then using a large fork, roughly smash everything together until a chunky sauce forms.
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4
Preheat oven to 350 degrees F.
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5
Cut each squash in half crosswise. Using a melon baller, carefully scoop out squash flesh, (reserve for the filling) leaving about 1/4 inch flesh intact on all sides and leaving squash closed at the bottom of each half. Keep the tubes in cold salted water until ready to use.
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6
Heat oil in a heavy skillet over medium heat. Add onions and cook, stirring with a wooden spoon, until they are soft and translucent, about 3-5 minutes. Add garlic and cook for 2 minutes more. Add the squash flesh, shredded carrot, celery, cumin, coriander and red pepper flakes and cook 8 to 10 minutes more.
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7
Deglaze with the wine and cook until the wine is cooked out about 5 minutes. Add rice, 1/2 of the roasted tomato sauce and cook an additional 3-5 minutes. Remove from heat and stir in pine nuts, parsley and mint. Let mixture cool slightly, about 10 minutes. Meanwhile remove the squash halves from the salted water and drain them well. Using a small spoon or clean hands, gently stuff the squash halves with the mixture.
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8
Place the squash halves tightly standing-up in a deep glass baking dish; pour the remaining tomato sauce all over the squash. Cover tightly with foil and place in oven. Bake for about 40 minutes or until the rice is soft and the squash is cooked through but still slightly firm.
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9
Note: If you don't have a deep glass baking dish, place the squash halves in a 9 by 13-inch glass baking dish; pour remaining tomato sauce all over the squash. Cover tightly with foil and place in oven. Bake for 20 minutes. Remove from oven, uncover and turn over squash. Re-cover, return dish to oven and bake an additional 20 to 25 minutes, until the rice is soft and squash is cooked through but still slightly firm.
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10
Serve hot or at room temperature with additional tomato sauce and a dollop of sour cream, creme fraiche or Greek yogurt.
