1. Preheat oven to 400°.
2. Cook pasta according to package directions, omitting salt and fat; drain and set aside.
3. Place asparagus and tomatoes on a jelly-roll pan. Drizzle with 1 tablespoon olive oil; sprinkle with 1/4 teaspoon salt and 1/4 teaspoon black pepper. Toss gently to coat; arrange asparagus and tomato mixture in a single layer. Bake at 400° for 6 minutes or until asparagus is crisp-tender. Remove asparagus from pan. Place pan back in oven, and bake tomatoes an additional 4 minutes. Remove tomatoes from pan; let asparagus and tomatoes stand 10 minutes. Cut asparagus into 1-inch lengths; halve tomatoes.
4. Combine shallots and the next 4 ingredients (through honey) in a small bowl, stirring with a whisk. Gradually add remaining 3 tablespoons oil, stirring constantly with a whisk. Stir in remaining 1/8 teaspoon salt and 1/4 teaspoon black pepper.
5. Place pasta, asparagus, tomato, olives, and arugula in a large bowl; toss. Drizzle juice mixture over pasta mixture; toss. Sprinkle with cheese.