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This cut of pork can be very lean, so take care not to overcook it or it will be dry. Ideally, it should still be a little pink in the center.
Preheat oven to 425°F. Heat 1 tablespoon of 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 to 8 minutes. Transfer skillet to oven and cook pork until an instant-read thermometer inserted in thickest part registers 140°F, 10 to 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 of chopped cilantro, and remaining 2 tablespoons of 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.