Preheat your oven to 400 degrees F.
In a baking dish, place the halved grape tomatoes along with 2 teaspoons of olive oil. Sprinkle with half of the salt and pepper.
Bake the tomatoes for 15 to 20 minutes, until they are "burst" and slightly blistered on the outside.
Meanwhile, toss the trimmed asparagus with the remaining olive oil, salt, and pepper in a medium mixing bowl.
Once the tomatoes are blistered, add the prepared asparagus to the baking dish.
Drizzle with balsamic vinegar and toss with the tomatoes.
Bake another 5 minutes until the asparagus is tender-crisp.
