Add the dates, tomatoes, chipotles, garlic, honey, and 1 tsp salt to your blender. Puree until very smooth. Pour into a deep saucepan and cook over medium-low heat for 5-6 minutes, add ¼ cup water halfway through and stirring. Cool, then reserve 2 cups for the chicken wings. Store the rest in an airtight container in the refrigerator for another use.
Preheat your oven to 450 F.
Season the chicken wings with salt on both sides. Drizzle some oil into a 12-inch oven-safe cast-iron skillet and place the skillet over medium-high heat. Lightly brown the chicken wings on both sides. You’ll likely have to work in batches for this. You don’t need to get thorough browning here, you just want to see some color.
Once all the wings have been browned, place them all in the skillet, squeezing them to fit however you need to (doesn’t really matter), then pour 2 cups of the date-chipotle mixture over them. Toss to make sure everybody’s well coated in the sauce. Lower the heat to medium and cook the wings about 10 minutes, turning and basting occasionally.
Place the skillet in the oven for 5-7 minutes, until the chicken is sticky and starting to laquer, and cooked through. Serve hot with lots of napkins.