Bring a large pot of salted water to a boil and cook the tortellini until al dente according to package instructions; drain and set aside.
Heat olive oil in a large skillet over medium-high heat.
Season the steak cubes with salt, black pepper, garlic powder, and smoked paprika.
Add the seasoned steak to the skillet and sear for 3–5 minutes until nicely browned; remove and set aside.
In the same skillet, melt the butter over medium heat and add the minced garlic. Sauté for about 1 minute until fragrant.
Pour in the heavy cream and whole milk, stirring to combine; let it simmer gently for 3–4 minutes to thicken slightly.
Gradually whisk in the parmesan until smooth and the sauce is creamy.
Add the cooked tortellini and seared steak back into the skillet and gently toss until everything is coated in the creamhouse sauce.
Taste and adjust seasoning if needed.
Sprinkle with chopped parsley, cracked black pepper, and red pepper flakes before serving.