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Preheat a cast-iron ridged grill pan. Brush the asparagus spears with 1 tablespoon of the olive oil and season with freshly ground black pepper, then place in the pan with the cherry tomatoes. Grill for about 8 minutes, turning a few times, until tender and lightly charred. Remove and keep warm. (If you don't have a ridged grill pan, cook the vegetables on a rack under a preheated medium grill.)
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