Preheat oven to 350°F. Line baking sheet with foil and coat with cooking spray. Place squash cut-side down on prepared baking sheet, and tuck garlic cloves in hollow under squash. Bake 50 minutes, or until tender. Cool 10 minutes. Scoop flesh from shell, and place in large bowl. Peel garlic cloves.
Heat large pot over medium heat, and coat with cooking spray. Add onion, and cook 7 minutes, or until translucent. Add ginger, allspice and cinnamon, and cook 1 minute more. Stir in squash, garlic, broth and 3 & 1/2 cups water. Bring to a simmer, and reduce heat to medium low. Partially cover pot, and simmer 25 minutes. Purée in blender or food processor until smooth. Serve hot or cold, and stir in chives and vinegar just before serving.
Place sugar, cornstarch, and salt in saucepan, and gradually whisk in coconut milk. Bring mixture to a boil over medium-low heat. Cook 5-10 minutes, or until thickened, whisking constantly. Turn off heat, stir in vanilla, then banana slices.
Line bottom of 11- x 7-inch baking dish with 24 cookies. Spread hot pudding over top, making sure bananas are submerged to prevent browning. Top with remaining 24 cookies, cover with plastic wrap, and cool. Refrigerate until cold. Top with whipped topping (if using).
Cook jasmine rice according to package directions.
Meanwhile, heat a deep skillet or wok-shaped pan over high heat. Add oil and crushed red pepper, and let sizzle for 10 to 15 seconds. Add eggplant, and stir-fry for 2 to 3 minutes. Add onion, bell pepper and garlic, and stir-fry for 3 minutes more. Add vinegar and soy sauce. Sprinkle with sugar, and toss for 1 or 2 minutes longer.
Remove pan from heat, add basil leaves and toss to combine with eggplant. Serve over hot cooked rice.