Rub pork chops with 2 tablespoons olive oil and sprinkle with 1/2 teaspoon salt and pepper on both sides. Cover and allow to sit at room temperature for 20 minutes.
Oil the grate of a grill and set to medium heat. Add chops and grill for 20 minutes, flipping halfway through. Internal temperature taken with a meat thermometer should read 145 to 160 degrees.
Toss the asparagus in 1/2 tablespoon olive oil, 1/4 teaspoon salt, and 1/4 teaspoon pepper. Add alongside the pork chops, after the chops have cooked for 15 minutes.
Thread cherry tomatoes onto skewers and drizzle with 1/2 tablespoon oil and sprinkle with 1/4 teaspoon of salt and pepper.
Grill asparagus and tomatoes for about 5 minutes, until asparagus is slightly tender and tomato skins have blackened a bit in places. After removing pork chops from grill, allow to rest 5 minutes before serving.
Cover veggies until ready to serve. Tomatoes may be served on skewers or removed from skewers.
Serve asparagus and tomatoes alongside pork chops and drizzle with pesto.
Enjoy!
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