Preheat oven to 400ºF.
Place a large sauce pot over medium high heat, add EVOO. Add the ground turkey and season with salt and pepper. Cook the turkey while breaking up with the back of a wooden spoon until browned and cooked through, about 5 minutes.
Add chili powder, cumin, grill seasoning, jalapeño (if using), onion and Worcestershire sauce and cook for 3-4 minutes or until onions are slightly soft. Add the diced tomatoes with their juice and simmer over low heat for 20 minutes then cool the chili. Once the chili is cool, stir in the cheese and reserve the mixture for filling. While chili is simmering, Mix up the sour cream with garlic and chives and reserve for dipper.