Step 1: Cut the top stems from the fennel, then slice the fennel in half lengthwise to expose the core. Remove the core and discard, then cut the fennel into very thin strips.
Step 2: Heat 1/2 tablespoon of the olive oil in a pan over medium heat. Add the fennel to the pan and do not stir. Once the fennel turns brown on one side, turn it over and allow it to brown on the other side.
Step 3: Add 1/4 teaspoon of the black pepper and the sugar and toss to coat.
Step 4: Add the half-and-half and bring the liquid to a simmer. (DO NOT BOIL) Remove from the heat and set aside.
Step 5: Mix the calamari with the salt, 1/4 teaspoon black pepper, garlic powder, red pepper flakes, and flour until well coated. Heat 1/2 tablespoon of the olive oil in a pan over medium-high heat. Add the calamari and cook 2-3 minutes, or until done.
Step 6: Add the calamari to the fennel sauce. Bring gently up to heat and serve.
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