Dry the halloumi. Pat the halloumi dry with paper towels. Set on a paper towel and covered with another sheet of paper towel to absorb as much moisture as possible while you prepare the other ingredients.
Prepare the Honey-Rosemary Glaze. In a small mixing bowl, mix together the rosemary, honey, and a pinch of salt and chili flakes (if using).
Prep the tomatoes. In a medium mixing bowl, combine the olive oil, dried oregano, and a pinch of salt. Wash and dry the cherry tomatoes, then add them to the bowl and toss to coat. Skewer 4-5 whole tomatoes on each skewer. Set aside, reserving any olive oil and oregano left in the bowl.
Get ready to grill. Preheat the grill to medium-high heat with the lid off. Remove the paper towels from the halloumi and brush both sides with extra virgin olive oil to prevent sticking. Pour over any extra oil that was reserved from the tomato bowl.
Grill the tomatoes. When the grill is hot, place the tomato skewers on one side of the grill, leaving room to add the cheese later. Cook the tomatoes for 10 minutes, turning until soft (but not quite fully charred yet).
Grill the cheese. Leaving the tomatoes on the grill, add the halloumi cheese. Grill for about 3-4 minutes on each side. Use a metal spatula to help loosen the cheese from the grill before flipping it.
Glaze. Once the cheese is crispy and the tomatoes are blistered and very soft, remove them from the grill and place them on a platter. While still warm, drizzle on the Honey-Rosemary Glaze and squeeze over the juice from the ½ lemon. Serve immediately with crusty bread.
