Bring a large pot of salted water to a rolling boil. Add the cheese tortellini and cook according to package instructions, usually about 3-5 minutes, until tender. Drain and set aside.

In a skillet over medium-high heat, drizzle olive oil to coat the pan. Season the steak with salt, black pepper, garlic powder, and smoked paprika. Sear steak for about 3-5 minutes until browned. Transfer to a plate to rest.

Lower the heat to medium, melt butter in the same skillet, and sauté minced garlic for about 1 minute until fragrant.

Pour in heavy cream and whole milk, stirring to combine with the butter and garlic. Simmer to thicken for about 3-4 minutes.

Gradually stir in the shredded Parmesan cheese until melted. Adjust seasoning with salt and pepper.

Combine seared steak and cooked tortellini in the skillet, gently tossing to coat in the sauce. Cook for another 2 minutes.

Garnish with parsley, red pepper flakes, and cracked black pepper. Serve immediately.