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Warm the oil in a medium pot over medium-low heat. Add the celery, fennel, onion, oregano, salt, black pepper, and red pepper flakes. Cook, stirring often, until the vegetables are soft, 8 to 12 minutes. Stir in the garlic and cook until fragrant, about 1 minute. Add the wine and cook until the liquid is almost completely reduced, 2 to 4 minutes.
Add the broth and bring to a boil. Reduce the heat to a gentle simmer and stir in the lentils, fregola sarda, and parsley stems. Cook uncovered, stirring often to make sure nothing sticks to the bottom of the pot, at a low simmer until the lentils are tender and the pasta is al dente (soft but with a chewy bite), 20 to 30 minutes.
Just before serving, stir in the parsley and any celery leaves, fennel fronds, tarragon, and chives. Grate or shave Pecorino atop (if using), and serve hot with lemon wedges on the side.
Store in a tightly covered container in the refrigerator for up to 3 days or the freezer for up to 3 months. The soup will thicken as it sits; add water or broth when reheating and an additional handful of fresh herbs before serving.