Preheat the oven to 350 degrees F. In a Dutch oven or oven-proof skillet, heat the olive oil over medium heat. Add garlic and red pepper flakes. Stir until garlic is softened, about 30 seconds. Add broccoli florets and season with salt and pepper. Cook, stirring often until broccoli is wilted, approx 2 minutes. Remove from heat and allow to cool.
In a large bowl, whisk eggs, milk, salt, and pepper to taste. When the broccoli mixture has cooked, add to the egg mixture along with the bread and 1/2 cup of parmesan. Stir well to combine. Lightly grease the Dutch oven or pan, and transfer the mixture to it. Top with bacon and more parmesan.
Place in the oven and bake until puffed, browned in spots and the center is set, 45-55 minutes.
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