4 garlic cloves, peeled
2 tablespoons olive oil, divided
1 package (10 ounces) refrigerated spinach tortellini
1 cup mayonnaise
1/4 cup grated Parmesan cheese
1/4 cup milk
1/4 cup prepared pesto
1/8 teaspoon pepper
1 pint grape tomatoes
26 frilled toothpicks
Place garlic cloves on a double thickness of heavy-duty foil; drizzle with 1 tablespoon oil. Wrap foil around garlic. Bake at 425° for 20-25 minutes or until tender. Cool for 10-15 minutes.
Meanwhile, cook tortellini according to package directions; drain and rinse in cold water. Toss with remaining oil; set aside.
In a small bowl, combine the mayonnaise, Parmesan cheese, milk, pesto and pepper. Mash garlic into pesto mixture; stir until combined.
Alternately thread tortellini and tomatoes onto toothpicks. Serve with pesto dip. Refrigerate leftovers.