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Preheat oven to 375 F. Spray one 8×8-inch baking dish or 4 single-serving baking dishes with canola oil or non-stick spray. (You may try cutting parchment paper to fit the pans instead.)
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Unroll the thawed phyllo dough and place it on your workspace. Remove one sheet and place it on a cutting board or other work surface. Place one peeled banana along one of the narrow ends, sprinkle the dough evenly with a fourth of the almonds. Sprinkle the banana with a dusting of cinnamon and then roll it up in the phyllo. Place it seam-side down in the baking dish. Repeat with remaining bananas.
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Give the tops of the wrapped bananas a quick spray with canola oil. Bake for 20-30 minutes, until tops are golden brown and bananas have begun to sizzle and release syrup.
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Drizzle with as much Chocolate Sauce as desired. For best results, serve immediately.
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For Sauce:
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Place the chopped dates in a bowl and pour the boiling water over them. Allow them to soak for about 10 minutes. (Note: Some dates are not as soft as others–soak them longer.)
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Place dates and water in blender container along with remaining ingredients. Blend until smooth, scraping down sides of container a couple of times to ensure everything gets blended.
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Refrigerate and use as needed.