Meanwhile, toss the asparagus with 1 tablespoon oil and sprinkle with salt and pepper. Place the tomatoes in a large sheet of heavy-duty foil. Toss with the remaining tablespoon oil. Sprinkle with salt and pepper. Fold and seal to form a pouch.
Grill the pouch of tomatoes until they char slightly and some burst, about 13 minutes. Grill the asparagus next to the tomato pouch, turning, until charred and tender, about 8 minutes.
Transfer the asparagus to a serving platter. Carefully open the tomato packet and pour the tomatoes with their juices all over the asparagus. Top with the olives.