Bring a large pot of salted water to a boil and cook the ravioli according to package directions; drain in a colander and set aside.
Heat the olive oil in a large skillet over medium heat.
Add the grape tomatoes and cook, stirring occasionally, until they begin to burst, about 3 to 4 minutes.
Add the minced garlic to the skillet and cook for 1 minute until fragrant, stirring so it doesn't burn.
Reduce heat to low, add the drained ravioli, and gently stir in the pesto until the ravioli are evenly coated and heated through.
Serve warm topped with grated Parmesan, fresh basil, and crushed red pepper flakes if desired.