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Pork Tenderloin with Date and Cilantro Relish

['3 tablespoons olive oil, divided', '1 pork tenderloin (about 1 1/2 pounds)', 'Kosher salt, freshly ground pepper', '2/3 cup Medjool dates (about 4 ounces), cut into small pieces', '2 tablespoons fresh orange juice', '3 tablespoons chopped fresh cilantro plus leaves for serving']

Preheat oven to 425°F. Heat 1 tablespoon oil in a large ovenproof skillet over medium-high heat. Season pork with salt and pepper and cook, turning, until browned on all sides, 6–8 minutes. Transfer skillet to oven and cook pork until an instant-read thermometer inserted in thickest part registers 140°F, 10–15 minutes. Transfer pork to a cutting board and let rest at least 5 minutes before slicing; set aside pan drippings.
Toss dates, orange juice, reserved pan drippings, 3 tablespoons chopped cilantro, and remaining 2 tablespoons oil in a small bowl; season with salt and pepper. Spoon relish over pork and top with cilantro leaves.
DO AHEAD: Relish (without pan drippings) can be made 4 hours ahead. Cover and chill. Add pan drippings just before serving.

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