Preheat your oven to 425 degrees and line a baking sheet with foil. Set aside.
Bring a medium pot of salted water to boil.
While you're waiting on the water to boil, coarsely chop the broccoli, mince the shallot, halve the grape tomatoes, and coarsely chop the parsley.
Place the chopped broccoli on your prepared baking sheet and drizzle 2 teaspoons of olive oil over the top. Season with salt & pepper then toss to coat. Spread into a single layer and roast for 12-15 minutes or until the broccoli softens and starts to brown. Remove from the oven and set aside.
Cook the pasta in your boiling water and cook 9-11 minutes, or until al dente. Drain and set aside. Bring the pot back to the stove.
Over medium high heat, add a teaspoon of olive oil and the minced shallot to the pot. Cook for 2 minutes.
Add in the evaporated milk and cook for 2 minutes.
Stir in the cheddar and asiago cheese and season with salt & pepper. Stir until melted the pour in the cooked pasta.
Line another baking sheet (or the same one, once you move the broccoli off) with foil and lay out the naan bread. Spread the macaroni and cheese evenly over the two pieces.
Top with roasted broccoli and grape tomatoes.
Sprinkle the panko crumbs over both flatbreads and drizzle 1 teaspoon olive oil over each.
Bake 9-11 minutes or until lightly browned.
Once done, sprinkle with chopped parsley and cut into desired number of pieces. Serve immediately.